Twenty Five Days To Mend A Broken Heart
by Lolsome-o-sis girl
Summary: [AU Fic] Castiel and Jimmy travel back to their hometown of Lawrence to celebrate their older brother Gabriel getting hitched. Of course, staying with the Winchesters means staying with Dean, Cas' high school boyfriend whom he did not exactly part on good terms with, which leads to angst, awkwardness, and a possible opportunity to fix two broken hearts, all in twenty five days.
1. December 1st: Castiel, Sam

**Twenty Five Days To Mend A Broken Heart**

 _Fandom: Supernatural_

 _Rating: T_

 _Genre: Romance_

 _Pairing: Dean/Castiel, Sam/Gabriel, Jimmy/Amelia_

 _Summary:_ _[AU Fic]_ _Castiel and Jimmy Novak travel back to their hometown of Lawrence_ _to_ _celebrate their older brother Gabriel getting hitched_ _. Of course, staying with the Winchesters means staying with Dean, Cas' high school boyfriend whom he did not exactly part on good terms with, which leads to angst, awkwardness, and a possible opportunity to fix two broken hearts, all in twenty five days. Destiel, Sabriel and Jimmy/Amelia MULTICHAPTER._

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 **AN: Hey there, my little sock puppets! I bring a new story for Christmas! (In fact I bring several Destiel stories for Christmas, but this is the only multi-chapter one, but I digress). Let's enjoy twenty five days of Destiel together, and see if we can mend their broken hearts! :) X**

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 **DISCLAIMER. I do not own Supernatural. Never have, never will. *single tear*.**

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 _ **December 1st: Castiel, Sam**_

 **Castiel.**

 **[You have one saved message.** **Received** **at 3.23 PM on November 19th 2015]**

 _"Uh, hey, Cas. It's Sam. Um, Sam Winchester? I don't know if you really remember me - I mean, it's a while since we spoke; I think I was around fourteen the last time we saw each other? Gabriel's said that he's mentioned me before though. I'm, um, I'm his boyfriend - What? Yes, Gabe, I know -_ _ **Ow!**_ _What was that for? Sorry, Cas, Gabe got a little over excited there...Anyway, I, um, I know we haven't exactly kept in regular contact over the years, but this, uh, this is pretty big, so I thought I should call you and let you know that Gabe and I are_ _...well, we're getting_ _hitched...Hooray! - What? Gabe, I'm_ _ **trying**_ _to talk to_ _ **Cas**_ _, so_ _ **shush**_ _. Sorry_ _about that_ _, Cas. Again. But, so, um, yeah, Gabriel and I decided to celebrate over Christmas, and I know that we haven't spoken in years, and I kind of understand why that is, but I'd really like it if you and Jimmy came down to Lawrence for the holidays. I mean, it's been, what? At least seven years since we last saw each other_ _?_ _That's over half a decade, y'know, man? I'd love to catch up with you guys again, find out what you've been up to all these years. Jimmy used to email Gabe every so often, but even he fell off the radar eventually - I guess that's just how it goes_ _. You move on and you change._ _Still, I think it would be fun for us all to hang out together again; I_ _really_ _miss that, y'know? I mean, we had some great times back in the day, didn't we? You, me, and D - Okay, I'm gonna stop there before I ruin any chance I ever had of persuading you to come. Just, give me a call back, yeah? Please? It...It would mean a lot to me - to_ _ **us**_ _\- if you guys were both there with us. Okay, well, I guess that's all I have to say, so...yeah. Bye, Cas. I hope to hear from you soon."_

Cas removed the phone from his ear with a sigh, tapping his fingers against the steering wheel of his car as it idled in the parking lot of the gas station, watching Jimmy and Amelia through the window of the Gas n Sip, probably bickering good naturedly over something trivial and mundane that Cas didn't really understand or have time for. He still wasn't entirely sure why he had even shown Jimmy the message that Sam had left on his voicemail, instead of deleting it the moment that he got it, which was what he should have done. It wasn't like he'd wanted to pick up the phone in the first place anyway; as soon as he recognised the number, he'd sent it straight to voicemail.

But, no. Something inside of him had made him let Jimmy take a listen, and now, thanks to that, here he was: stuck behind the wheel of the ancient car that had been in his family since the sixties and that wheezed every time it went round the slightest corner, waiting for Jimmy and his long-term girlfriend to get out of the store so that they could get on the road towards the Winchesters' place. It was almost like he was under the absurd impression that the sooner that they got there, the sooner they could leave again and retreat back to the safety of Pontiac. Cas was already missing his home comforts, already looking forward to returning to his apartment with its bright yellow walls and less-than-glamorous view of a Biggerson's family restaurant and its adjoining parking lot.

Jimmy banged noisily on the car roof, startling Castiel from his wistful thoughts of Illinois and the place that he had come to see as home. He sent a fowl glare in his twin's direction.

"Are you purposely trying to give me heart failure before we get to give Sam and Gabriel our blessings, Jimmy?"

"Blessings? Huh!" Jimmy pulled a face. "I'm giving the guy more than that; I'm giving him my _prayers_! He's gonna need it now that Gabe's gonna actually be part of the Winchester clan."

"Now, really, Jimmy," Amelia began, shaking her head as Jimmy climbed into the back seat beside her. "I think you're exaggerating sometimes when you talk about Gabriel."

Cas smirked. "Oh, just you wait and see. You might think that Jimmy and I are strange, but just wait until you meet Gabriel."

"Trust me, babe. You can't ever go back from it," Jimmy added.

"I'm sure I'll cope," Amelia replied with a roll of her eyes. "You Novaks can't be too dissimilar."

"Well, I suppose that's true. I mean, if you've put up with Jimmy for this long - Ow!" Jimmy had leaned forward to give him a whack on the back of the head. "What was that for?" He shook his head as he pulled out of the Gas N Sip parking lot, his car grumbling and groaning about it the entire time, turning onto the highway. Not too far up ahead, the familiar sign was nailed into the ground.

 _ **LAWRENCE, KANSAS, WELCOMES YOU.**_

The message on the sign was a lie, for him at least. For Castiel Novak, there didn't seem to be anything remotely welcoming left in Lawrence, Kansas.

* * *

 **Sam.**

"Stop fidgeting, Samsquatch. Sheesh, you're making me nervous."

Sam rested his hands over his slacks, silencing the drumming his fingers had absentmindedly been making on the patch of material. "Right. No fidgeting. Gotcha."

Gabriel tutted from the seat beside him at the kitchen table. "Honestly, man. Anybody would think that it was the police comin' to arrest you for something, not my two dorky twin brothers comin' for Christmas."

Sam exhaled loudly. "I know, I know. It's just...well..."

"It's just, what?" Gabriel prompted when he trailed off.

"We haven't exactly kept in contact with them, have we? It's already gonna be awkward as it is - y'know, considering that we didn't exactly part on the best of terms..."

" _We_ didn't? Sam, what happened back then has nothing - and I mean, _nothing_ \- to do with us, okay? It was our stupid brothers who chose to break up and hold pointless grudges against each other for it."

"But, that's exactly what I'm talking about, Gabe. What happens if seeing each other again after all this time sparks this whole thing off again? You know as well as I do how Dean reacts every time we even mention the names _Castiel_ or _Novak_ in the same room as him."

"Samwich." Gabriel fixed him with a serious look, which was a rare thing for him. "Seriously, I get it, okay? You're worried about Dean - and that's understandable, yeah? He's your brother and you love him. I feel the same way about Cassie. Apparently he hasn't spoken about what went on between him and Dean to anyone, not even Jimmy, since they broke up. But this isn't about them, is it? This is about us, yeah? Us getting married and finding happiness together - and yes, I know that sounds sappy as hell, but I'm tryin' to make a point here - and if those two idiots can't keep their personal post-break up pining and angst to themselves, well...I'll break their jaws for them."

Sam raised his eyebrow at the threat, but he also felt his mouth twitching into a smile. "You really are an awful boyfriend, Gabe."

"It's _fiancée_ now, thank you very much," Gabriel corrected, nuzzling what little of Sam's shoulder he could reach. "But you love me for it."

Sam let out a hum, sliding an arm around him. He couldn't argue with that. "You've got a point there. I do."

"I should hope so when you recently agreed to let me join your family properly - especially when I went to all the effort of cooking you that big romantic dinner."

Sam smirked. "I see. So pancakes and syrup now count as a _big romantic dinner_ , do they?"

"Oh, don't lie, you loved it."

Sam would have given him another sarcastic reply, even though he _had_ loved it, very much, but he was cut off by the sound of someone knocking on the front door.

Gabriel grinned. "I think the Novaks have just returned to home soil, don't you Samsquatch?" He pulled Sam up from his chair and dragged him towards the front door, practically wrenching the door off its hinges in his haste to get it open. The younger Winchester felt a grin of his own splitting across his face as he took in the sight of the dark-haired blue-eyed man on his doorstep, wearing a grubbier, yet better-fitting version of the long tan trenchcoat that he remembered so well.

"Cas," he said, voice filled with recognition.

"Hello, Sam," he replied, causing Sam to let out a startled chuckle. Had Cas' voice always been that gruff? "It's been a long time."

"Too long," Sam agreed earnestly. "You're looking well, man."

"Thank you. You too."

"C'mere, Cassie, you dark horse!" Gabriel smirked, enveloping his younger brother into a bear hug.

"Gabriel," Cas greeted stiffly, looking less pleased to see him again compared to Sam.

Gabriel released him gleefully. "Where's Jimmy got to? I thought you said that he was coming to."

"He's by the car right now." Cas gestured down the garden path to the sidewalk, where two figures stood, illuminated by the lights coming from the neighbourhood houses, talking amongst themselves. "He's insisted on carrying all of the bags himself. I think he wants to impress Ame -"

"Jim-Bob!" Gabriel took off down the path, carelessly disregarding the fact that it was a freezing cold night and he was wearing nothing more than a t-shirt and jeans (Sam hoped that he wouldn't get himself sick, because obviously it would be his responsibility to look after him and he would get sick himself), hurling himself at Jimmy the same way he'd embraced Cas, walking back up the garden path with his arm tucked comfortably over his brother's shoulder with a spring in his step.

"Look at us," he beamed. "The old team back together. Well..." He grinned at Amelia. "...with some new additions, I see." Sam noticed how he avoided any mention of the one missing part of their "old team", but he chose not to mention it. It was already so obvious; he saw Cas' shoulders tense at the very thought of it.

Amelia laughed suddenly, breaking through the tension. "Are you worried that I'll ruin your credibility?"

"You could never do that," Jimmy replied loyally, giving their interlocked fingers a squeeze.

Gabriel rolled his eyes. "I swear we aren't this touchy feely, are we, Samsquatch? Maybe we are and I just haven't noticed because I'm so absorbed in those big brown puppy dog eyes of yours." He threw Sam a wink, making Jimmy and Amelia snort simultaneously.

"Gabe." Sam let out a huff. "Let's not start that out here in the cold."

"Good idea." Gabriel clapped Jimmy on the shoulder and slipped inside the house, dragging Cas along with him (who went rather unwillingly, Sam noted). "Mama and Papa Winchester!" He was yelling up the stairs now as he bustled their guests into the living room. "We've got visitors!" He collapsed down on the couch, as if the whole act of greeting people tired him out, pulling Jimmy and Amelia down with him so that Jimmy was sandwiched in the middle. Cas remained by the door, watching the scene unfold with his hands in his trenchcoat pockets.

Sam sent him an apologetic look. "Sorry about that."

Cas glanced in his direction, looking a little surprised that Sam was even talking to him at all. "About what?"

"Letting Gabe go all brotherly on you. You didn't look very comfortable."

"Don't worry. I remember from childhood experience exactly how Gabriel can be."

"It's just..." Sam paused. "I don't want you to be uncomfortable here. It's been ages since we've seen each other, y'know, and I really want you to feel welcome here and -"

"That's very kind of you, Sam," Cas replied, cutting him off with something that might have been a smile. "I really appreciate it - I do - but I think we both know what the elephant in the room is here and that it can't just be avoided."

"I know. I just -" He was interrupted again, this time by footsteps clattering across the landing and down the stairs. A moment later, his parents appeared in the doorway, Mary in front with John just a few steps behind.

Mary let out a yelp of surprise, before a smile spread across her face. "Castiel!" She swept him up into a warm hug. "Look at you! You're all grown up now, love!"

"Hello, Mrs Winchester, Mr Winchester," Cas greeted politely, as John gave him a pat on the shoulder as a form of greeting. John wasn't big on hugging and affection with anyone other than his wife; Sam had long since realised that this was a trait that had been passed on to Dean, but had thankfully by-passed him.

"Oh, stop that." Mary gave him a gentle poke as she released him, placing a gentle peck on his cheek, the same way she had always done when they were all children. "It's Mary and John to you, Cas, just like it always has been." She glanced around the room, another smile breaking out on her face when she saw the other Novak twin. "Jimmy!" She moved across the room to hug him too. "Look at you - look at you both! You both grew up so handsome! And clearly I'm not the only one who's noticed." She extended an arm around Amelia as well. "This one's a keeper, dear, take it from me. I've known him since before he could walk." She grinned suddenly. "I may even have some photos somewhere."

"Mary!" Jimmy shifted, looking uncomfortable, causing the others to laugh and John to try and disentangle his wife from their new house guests. The other Novak twin cleared his throat and quickly tried to move the conversation away from him and the possible photographs of him as a toddler that Mary might have stashed somewhere (knowing his mother, Sam reckoned that this was probably true).

"So," he said. "I hear that you guys are getting hitched, Gabe."

"You'd better believe it, Jim-Bob." Gabriel flashed Sam an adoring look that made him grin, despite himself. "I'm gonna make an honest man outta my Samwich."

"Are you sure that it isn't the other way around?" Jimmy quipped.

"Are you implying that I'm the wife in this relationship?"

"You mean you didn't realise that before?" Sam snorted, rousing laughter from everyone else in the room, even Cas, who had probably been looking sullen from the moment that he left Illinois. The sound was so cheerful, so homely, that Sam almost forgot to panic when he heard the front door opening.

Almost forgot.

"Hey, Sammy?" The familiar voice called from the hallway, causing the merriment in the room to subside sharply and immediately as Dean's footsteps got closer to the door. "Okay, I get that Gabe eats like food's gonna go out of fashion tomorrow or somethin' but, seriously, did you really need me to buy all o'this stuff - ?" He stopped mid-sentence, practically freezing as he stepped into the room, his eyes meeting Cas' blue iris almost instantly. John opened his mouth, going to say something, until Mary squeezed his arm, a silent plea to remain quiet.

Sam cleared his throat in the silence after a few minutes of hearing nothing but the second hand of the clock ticking away in the background. "Uh, hey Dean, you, um, remember Castiel and Jimmy, right? The, er, the Novak twins?"

"Yeah," Dean replied, a scowl finally forming on his face to coincide with his blunt words. "Don't think I'm gonna forget in a hurry." He finally pulled his eyes away from Cas and fixed them on Sam. "I'm gonna go put all this crap away, yeah?" He turned on his heel, striding out of the room and letting the door bang shut behind his retreating form.

Sam let out a sigh, watching as Cas' shoulders slumped, draining of tension. Who had he been trying to kid? Had he really been expecting Dean to see Cas again after all this time and somehow let go of all his grudges? Or, even better, jump on him and kiss him senseless - because Sam knew pining when he saw it, and he didn't want to spend another holiday season drowning quietly in Dean's brooding waves of angst.

But, unless he did something, and did this something fast, this was going to be the most uncomfortable Christmas he'd ever experienced.

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 **Well, that was that! I hoped you enjoyed December 1** **st** **.**

 **Until December 2** **nd** **, my little sock puppets... :) X**


	2. December 2: Castiel, Dean, Bobby, Jimmy

_**December 2nd: Castiel, Dean, Bobby**_ _ **, Jimmy**_

 **Castiel.**

"Hey, Cas." Sam glanced up from the plates of pancakes that he was serving up. "How d'you sleep?"

Cas slumped down at the breakfast table, dragging a hand across his eyes and letting out a groan. "Awful."

Once the general festivities and the Welcome Back To Lawrence dinner of the previous evening were over, inevitably the subject of room allocations came up in the conversation - in a house with four bedrooms that had to hold eight people for the next few weeks, it was bound to become an issue at some point. Mary and John had their room, Sam and Gabriel had theirs, Jimmy and Amelia had been given the spare room, which of course meant that the only room that had any space left for Cas was -

Dean's room. Great. Just when he thought that this Christmas vacation couldn't get any more awkward.

Amelia had offered to let him sleep in the spare room with her and Jimmy, insisting that they didn't mind, really, and Cas had almost agreed until he saw his twin brother's face that told him that he _would_ mind, thank you very much. Which was how Cas ended up curled up under a blanket on the hard wooden floor of Dean's bedroom, pretending to be asleep when he heard the elder Winchester come in, cursing expressively under his breath before he got into his own bed and rolled over so that he had his back to him. Which was absolutely fine with Castiel, who wanted to avoid Dean as much as possible. Luckily, Dean had disappeared earlier that morning, up and out of the room without Cas even stirring from his light doze.

Sam gave him a sympathetic expression, sliding his breakfast across the table. "Sorry, man. I mean, I didn't think -"

"It's fine." Cas waved his apologies away. He couldn't think about the mess that his relationship with Dean had become, not right now, this early in the morning. Instead, he speared a chunk of pancake and popped it into his mouth, glancing around the kitchen as he did so.

"You kept it," he marvelled suddenly, eyes falling on a childhood crayon drawing still stuck on the side of the refrigerator, one that he himself had drawn one sunny afternoon during Kindergarten.

"Kept what?" Sam followed his gaze and then smiled when he saw the picture too. "Well, yeah, of course we did. You and Jimmy are part of our family, aren't you?"

"Are we?"

Sam looked baffled. "Yeah. Yeah, of course you are, Cas. You always have been. Didn't you know that?"

He shuffled. "I just thought - What with everything that happened with Dean -"

The younger Winchester let out a sigh, and shook his head. "Ignore Dean. Whatever he's got goin' on is his own problem. I know that he's my brother and I'm supposed to be on his side in all this, but I still don't get what exactly made him react, y'know, like _that_. I mean, college is...well, _college_ , right?"

Cas nodded his agreement as he took another bite of breakfast. He'd been thrilled when both his and Jimmy's acceptance letters to their chosen college in Pontiac had arrived in the mail, so much so that the two of them had danced around the kitchen, shrieking and hugging as they did so, sounding like a pair of giggling five year olds, and he'd been so certain that Dean would have been just as excited for him as he was. Weren't people who were dating supposed to be _happy_ for their significant other when something good happened to them?

Well, clearly not Dean, apparently. His face had fallen the moment that Cas had told him; it wasn't long before they had been yelling at each other and Cas was out of the front door and halfway down the street before the tears had started and Jimmy had caught up with him. That had been the last time that he had either seen or spoken to Dean, not even going to say goodbye when he left, for seven years - and now, here he was. Back in the house that had been his childhood home just as much as his parents' house had been.

"I don't know," he said now, in reply to Sam. "I guess he just didn't like the idea of me leaving town."

"Understatement," Sam snorted, a phrase that he had picked up from Jimmy years ago. "Gabriel!" He was calling towards the stairs now. "I made breakfast, and I'm not makin' you any more if it goes cold!"

"I thought you were supposed to be the loving fiancée, Samwich!" Gabriel yelled back. "I see I was wrong in that regard!"

Sam let out a mock gasp to match his faux wounded expression. Cas merely rolled his eyes.

* * *

 **Dean.**

"So, what's the reason that we're drinkin' ourselves into the ground this time?"

Dean flashed Jo a half smile. "What makes you think there's a reason? Maybe I just really fancied a beer this mornin'?"

"Yeah, right. Even you, Winchester, don't drink until after noon." Jo leaned over the counter to clap him on the back of the head. "C'mon, Dean, what's bitin' your ass? Talk to me."

Dean paused, taking a swig of his beer, clearing his throat as he did so. "Do you remember a guy called Castiel Novak, by any chance?"

"Novak...Novak..." The blonde's brow furrowed as she thought. "Uh, vaguely, I think. He was the little nerdy guy with dark hair and the beautiful blue eyes, right? The one that you used to go out with and all the girls were super jealous of you because of it?"

"That's the one."

"Yeah, yeah, he was the one with the twin who never stopped eatin'. I remember now. What 'bout him? You ain't mentioned him in years."

"Well, y'know Sammy's gettin' hitched, right? He invited those two chuckleheads to stay at ours over Christmas and Cas is now sleepin' on my floor -"

"And, let me guess, you'd rather he was sleepin' in your bed, right?"

"Jo!" Dean aimed a shove in her direction. " _No!_ "

"Well, what's this all about, then? I mean, I get that he left town and that, but you've been pissed at him for years. Why?"

"You'd be pissed too if the guy you lo - you were goin' out with suddenly turned up on the doorstep and was all _"Hey, babe. Sorry, can't stop, I'm leavin' town next week and forgot to mention this to you earlier. No big deal, right?"_."

Jo clucked her tongue as she thought. "I guess so. But, hey, at least he'll only be here for a couple o'weeks, right? Once the holiday's over, he'll be gone."

Dean hummed in agreement and took another drink from his beer. The sooner that Castiel Novak went running back to Illinois, the freaking better. Just the sight of him again made him feel all funny inside - something that he needed to put a stop to as soon as possible.

"You done your shoppin' yet?"

"Huh?"

"Christmas shoppin', Dean. You done it yet?"

Dean snorted. "What do you think? You know I don't do all that festive crap nowadays." Christmas had never particularly been his favourite holiday, hadn't been for a long time, not since he was a teenager. The last Christmas that he could truly remember being merry was roughly ten years ago, when the entire Winchester household had gone out for dinner with -

He quickly banished that thought from his mind. How the freaking hell did Cas Novak came up in everything he thought about? The quicker he left, the quicker things would return to normal, and the happier Dean would be for it.

"You're thinkin' 'bout Novak again, aren't you?"

"No!"

"Don't bullshit me. Your eyes go dilated whenever you think 'bout him. You know what that means, don't you?"

"Shut up." Dean tossed a couple of notes across the bar in order to distract the shit-eating grin starting to form across her face. "Whatever we had - or didn't have - is long gone."

"Uh hu," Jo replied, unconvinced. "Whatever you say, Dean. I'm not going to stop you from tryin' to live in denial for the rest of your life. Tell Cas to drop in sometime, though, if you're actually speakin' two words to him, and that twin of his too. I'd like to see both of those dumbasses again - plus, I need to officially offer Sam my congratulations and all that."

Dean nodded. "I'll tell him to call you," he replied, eager to hurry up and get himself away from Jo and her prying, all-knowing eyes.

* * *

 **Bobby.**

"What the hell you doin' here, boy?"

Dean rolled his eyes in Bobby's direction as the older man poked his head out from the office in the back of the garage. "Oh, well, hello to you too, Bobby. I'm havin' a great day, thanks, especially now that I've noticed that the King of Hell ain't here, how 'bout you?"

Bobby sent him a hard stare. "Don't take that sass with me, son, you know what I meant. It's ten o'clock in the mornin'; what're you doin' here so early?"

"Workin'," Dean replied with a shrug of his shoulders.

Bobby's eyes narrowed. "Your shift don't start until twelve."

"Am I not allowed to make social calls now? Sheesh, it's like that time I bought Sammy a cake all over again." Dean shook his head, his shoulders giving another shrug, trying to pass the situation off as nothing. "And, anyway, can't I just drop by an' help out of the goodness of my heart once in a while?"

Bobby shook his head. Dean only dropped by to " _help out of the kindness of his heart_ " when something was wrong back at the Winchester house that he didn't want to acknowledge was there. "Victor Henrikson bought his car in earlier. You can start takin' a look at that if you insist on bein' here so damn early, since Crowley hasn't bothered showin' his ass around here yet."

Dean gave him a grin, looking relieved that he had been permitted to stay - not, Bobby knew, that he would have listened if he told the boy to go back home for a few more hours - and peeled his jacket off, draping it over the nearby work bench and reaching for the wrench out of the toolbox.

Bobby knew why, of course. Sam had called him a few days before and warned him about the Novaks coming back to town. He often found himself sighing when he thought about the damn mess this whole business had become. Dean hadn't even mentioned Castiel in years, at least half a decade, but Bobby could clearly remember when those two idjits were joined at the hip. He'd lost count of the times he had wandered into the garage when Dean used to drop by after school and found those two seated around a car together, Cas watching everything his best friend did with some sense of awe and wonder, Dean explaining everything that he was doing and laughing when Cas tried to guess what was the best way to fix up the car. Sometimes, Bobby wondered where that cheerful, carefree smile had gone; he'd see flashes of it from time to time on adult Dean's face, but no where near as much as he had when high school sophomore Dean had been tinkering around in the garage with his best friend beside him.

Bobby hadn't actually asked about what had happened between them, before and after Cas and his brother had left town - it was none of his damn business, after all - but it must have been serious if it had wiped away that carefree smile the way that it had.

"Heard from Sam the other day," the older man began cautiously.

"Oh?" Dean had already poked his head under the hood of Henrikson's car. "What he say? He told you 'bout him and Gabe yet?"

"The happy couple? Pretty sure anyone with half a lick o' sense coulda seen this comin' for miles." Bobby snorted. "Nah, I'm talkin' 'bout your holiday guests."

"Oh. Them." Dean shook his head. "I'm tryin' to block it all out, to be honest."

"Dean -"

"Bobby, I don't wanna talk about it. Can we drop it? Please?"

"Okay." Bobby held up his hands, but his gaze was reproachful. "Whatever you want."

Dean smiled gratefully and went back to work.

"Idjit," the older mechanic muttered under his breath.

* * *

 **Jimmy.**

"Tell me, what does one get their irritatingly uptight twin brother for Christmas?"

Amelia chuckled, as Jimmy slid yet another book back onto the shelf. "No luck, huh?"

He let out a sigh. "You could say that." He reached for another book. " _Cupcakes In Cups_. Maybe this? It might make him better at cooking."

No one in their apartment building was going to forget the night that Cas tried to make some toast and ended up setting off the fire alarm and hailing the fire department, leaving everyone stranded outside in their pyjamas in the middle of a rainstorm. His twin brother had never made friends easily, but Jimmy was certain that it was a lost cause when the identity of the culprit was discovered. At one point he thought he was going to have to step in and break up a fight. Since then, he'd taken it upon himself to try and teach Cas the way of preparing food, and so far it hadn't resulted in much success.

"Not even my brother could mess up using a microwave, right?" He exchanged a look with Amelia, before both of them shook their heads, Jimmy placing the book back. "Yeah. Maybe not the best idea to let him near electricals. Better stick to cold cut sandwiches for now. Speaking of sandwiches..." He turned to glance imploringly at her. "Can we go eat now? I know this great place called the Roadhouse not far from here..."

Amelia shook her head again, but this time in fondness. "What about your brothers' Christmas presents? I thought the whole point you coming along with me was to get something for them."

"Do I really need to get Gabriel anything, though? I mean, c'mon, he's already got himself a fiancée this Christmas, I'm pretty sure he's done alright this year."

She gave him a gentle nudge with her elbow. "That doesn't count unless you're Sam."

Jimmy turned to glance back at the shelf. "Maybe I'll get the cookery book for Gabriel. He looks like he knows how to handle a microwave." He reached for it, and then paused. "Although, that being said, he did microwave a spoon once and blow the machine up."

"Are you sure that wasn't _you_?"

"Hey! I'm not that great at cooking, but I know how to use a microwave." After another moment of deliberation, Jimmy plucked the cupcake book from the shelf. "Sam'll just have to take the risk." He nodded once in confirmation, and slung a warm arm around Amelia's shoulders, letting her snuggle into his side. "What do you think of Sam, by the way?"

"He's...nice. They're all nice." Amelia hesitated for a moment. "Just Dean's a little...how do I describe it?"

"Bitchy?" Jimmy offered up.

"I was going to go for _intense_."

He rolled his eyes at the ridiculousness of it all. "It's only because he can't stand the fact that Cas and I are here. He didn't exactly take the news of Cas leaving for college very well."

"Why?"

"God knows. I didn't understand then when I went over to his house and threatened to do some damage to his face for breaking my brother's heart and I still don't understand now. All I know is that he can't stand the sight of us, even after all this time."

"I noticed. I saw him run into Cas in the hallway last night; he looked like he wanted to either lock Cas in the broom closet and then leave or jump in there after him and aggressively make out with him when no one else could see."

Jimmy snorted. "To be honest, Dean always looked at Cas like that a little bit. Except he didn't always look like he was capable of torturing puppies whilst doing it. That appears to be a new thing."

To say that the older Winchester was brooding over his twin brother would have been an understatement. Even Cas himself had noticed it, and Cas was known for being rather unobservant when it came to romantic advances. It had taken him three years to notice Dean's interest in him back when they were all teenagers in high school and then another six months before he admitted that he felt the same way. Locking them in the stationary cupboard in Ms Milligan's classroom had been one of the proudest moments of Jimmy's life so far, especially when Dean and his brother were eventually allowed to emerge and both of them looked more unkempt and rumpled than they had done when they went in.

"Stop that."

Jimmy turned to glance at his girlfriend, who now had her arms folded. "What?"

"I know that face. That's your scheming face. Cas warned me about that." The redhead added a smirk to her all-knowing expression. "What is it this time?"

"Nothing!" Jimmy insisted.

 _Well, nothing yet._

* * *

 **Well, that's all for December 2** **nd** **!**

 **Until December 3rd, my little sock puppets... x :)**


	3. December 3rd: Gabriel, Mary, Sam

_**December 3rd: Gabriel,**_ _ **Mary, Sam**_

 **Gabriel.**

"Okay, gentlemen," Gabriel announced as soon as he swept into the kitchen, a brightly coloured leaflet in his hand. Cas glanced up from the plate of toast Sam had placed in front of him that he was drooping over, reminding Gabriel of a wilted flower that needed watering - or maybe, Gabriel reasoned, his brother just needed sex. Who knew.

"What?"

"I've been doing a lot of thinking, Cassie, and I've realised that I can't just let you sit on the couch all day saying and doing nothing." Jimmy and Amelia had gone out to explore the sights of the Novaks' hometown, which meant that Gabriel had been stuck indoors with his moose of a fiancée to babysit his moping little brother. Thank God Dean had disappeared early and hadn't crawled back in until long after Cas had retired upstairs. Gabriel didn't need _that_ brooding ass getting in the way too; at least he was safely asleep right now due to a raging hangover. Served him right, really. Gabriel was the one who had been forced to put up with his pining for the past seven years. There was only so much that a man could take of being around a lust-fuelled grudge practically twenty four seven. Especially when the lust-fuelled grudge was over something as ridiculous as this. His brother had gone off to college, for Christ sake. What was the big freaking deal? Sam had gone to Stanford and Gabriel had patiently waited for him to return. (Well, maybe not entirely patiently, but a man could have slip-ups, right?)

"Gabriel," Cas began, looking up at him through his eyelashes, hardly able to keep his eyes opened, it seemed. "I really don't feel like getting caught up in one of your schemes -"

"Tough luck, Cassie. You don't get a choice in the matter." Gabriel pushed the leaflet towards his younger brother as he spoke. Really, this was for Cas' own good. He couldn't spend the entire night perched on the couch with his hands neatly resting in his lap whilst he stared mindlessly at the TV set that wasn't even on (again). As the older, much more responsible brother, Gabriel wouldn't stand for it.

"You remember the Harvelles, don't you?" He continued as Cas picked up the leaflet and took a glance at it. "Jo and Ellen? The ones that run the Roadhouse? Well, every year, they do some kind of fancy dress evening, and tomorrow night I'm dragging all of you with me. And, before you open your mouth, Cas, yes, Dean probably will be there too, and no, you're not getting out of it because of that."

"I really don't think that's such a good idea -"

"What did I just say about not getting out of it because of that?" Gabriel rolled his eyes heavenwards. Sometimes it felt like he was only rational one in the Novak family. Sure, Dean and Cas could try to avoid each other all they wanted, but it didn't change the fact that those two chuckleheads were still hopelessly in love with each other. Now that his twin brothers were back in their lives, Gabriel was eager to get the making up started and remove the fog of misery that had followed Dean - and, consequently, the rest of them - around like a loyal golden retriever.

"C'mon." He nudged Cas with his index finger. "We haven't spent any quality time together in years."

"There's a reason for that," Cas replied dryly.

Gabriel pursed his lips into a pout. His little brother really needed to remove that stick that was stuck up his ass. "Well, now you're just being mean. I was trying to do something nice, out of the kindness of my heart, and this is the thanks I get?"

Sam let out a snort from the other side of the room, having listened to the conversation quietly as he turned on the faucet and let the sink fill up with water, grabbing a damp dishcloth from the counter and hurling it in his fiancée's direction. "Gabe, leave him alone. If he doesn't want to go, don't make him."

Gabriel sighed. "You're supposed to be on my side in these things, Sam! I'm your husband, ish!"

"And _Cas_ is my friend," Sam replied, throwing a smile in Cas' direction, earning a look of gratitude in return.

"But he's _my_ brother!"

"And _I'm_ still in the room!" Cas interrupted.

Gabriel rolled his eyes. Castiel never used to require this much hard work and grovelling. "Look, Cassie, if you won't do anything tomorrow night, will you at least come out with us today? Once Sam drops off his paper for this week, we're gonna go get some lunch and try and get some fancy dress things. I promise I won't make you try anything on, not even a hat. You can just mock me and Samwich whilst we try things on, if you want to."

"Who says you're gonna make me try things on?" Sam asked with a smirk.

"Because you are my Samsquatch," Gabriel replied simply. "And we're supposed to do couple-y stuff together, right?" Although, not too couple-y. Gabriel loved Sam - well, obviously he did, or he wouldn't have mustered up the effort to make pancakes, which was more difficult than the little (or not so little) Winchester made it look - but he didn't fancy the idea of turning into the matching jumpers type, like Jimmy and Amelia (he was pretty sure that he saw them wearing matching socks yesterday). Thankfully, Sam didn't seem to want that either.

"We do couple-y stuff _now_ ," Sam pointed out. Cas let out a groan and clapped his hands over his ears.

"No, no, no, stop, stop it now," he announced loudly. "Please don't delve into the subject that I think you're talking about. Please."

Damn. Who would have guessed that Castiel Novak would have developed such a dirty mind since he'd been gone? All that time in Pontiac must have done him good.

"Relax, Cassie. There'll be no talk of that crap." Gabriel suddenly smirked. "Not that it _is_ crap, of course -"

"La la la la la!" Cas clamped his hands tighter over his ears. Sam simply stuck his tongue out, although there was a hint of redness dusting his cheeks. "I'm not listening to this!" His younger brother rose from his seat and all but sprinted out of the room, still trying to block out the sound of Gabriel's laughter.

Sam raised an eyebrow. "You're an awful big brother, you know that, right?"

"Oh, I know," his fiancée replied cheerfully. "I know."

* * *

 **Mary.**

"Dean?" Mary knocked on the door gently, pushing it open when she received no reply from her son. "Honey? You feeling alright?"

She got a mumbled groan in response, followed by a "Mom, don't talk so loud!". She shook her head, moving across the room, stepping over Cas' makeshift bed on the floor and settling herself at the bottom of the bed. Dean peered out of nest that he had made in the middle of the duvet, green eyes squinting against the dull light of the December morning.

"How're you feeling?" She asked again, a hand resting on his foot.

"Like I just got hit by a truck travellin' at a hundred miles a freakin' hour."

"Rough night, huh? You'd think you'd learn by now."

A half smile managed to find its way onto his face. "You'd guess so."

"So, what's bothering you, then? You only drink this much when you're trying to get your mind off something. What is it?"

"Nothin'," Dean replied, mumbling a little, not fooling Mary for a moment.

"And this "nothing" doesn't have anything to do with Castiel and Jimmy staying here with us, right?" She exhaled sharply, shaking her head. " _Dean_..."

"I know, I know. Please don't give me the bygones lecture again." Her eldest pulled the blankets up around his face even more, as if he could somehow escape her words in this way.

"Just, try to be nice? Civil, at least. Please. If not for Cas' sake -" This earned her a scoff "- or for mine, then do it for Sammy. He's getting married, and I'm sure he doesn't need to be worrying about this on top of everything else, yes?"

Dean considered this for a moment, before he sighed. "Okay. Fine. I'll try. For Sammy, and only for Sammy, because he's my brother."

"That's my boy." Mary reached out and gave his foot a gentle squeeze, something that made him let out a noise of protest.

"Mom, I'm not four anymore!"

"Believe me, sweetheart, I think I've realised." She squeezed his foot again, this time more teasing than comforting, before she rose from her seat and retreated back across the room, shutting the door behind her with a soft click, turning and almost barrelling head-first into Castiel who, for some reason, had his hands clamped over his ears.

"Oh!" Cas started, stumbling as he tried to avoid knocking into her. "Sorry, Mrs W - I mean, Mary."

She laid a hand on his arm. "It's fine. No harm, no foul, no bruise. How are you, Cas? Are you enjoying your stay?"

"Yes, it's lovely," Cas replied politely, a lie that Mary saw through almost immediately. That was the handy thing about knowing someone before they could walk; you picked up on all their little mannerisms.

"Well, that's good," she said aloud, choosing not to call him out on his white lie. "What are your plans for today?"

"Gabriel and Sam have decided that I need to get out of the house. They're taking me... _shopping_." He pulled a face at the word, making Mary chuckle. Apparently, Cas' awkwardness in social situations hadn't faded with age.

"I'm sure Sam will keep Gabriel on the straight and narrow."

"One can only hope so," Cas agreed.

"I hope that you boys have fun today." Her voice was earnest when she spoke.

"I doubt it," Cas replied, but he nodded, his eyes grateful as his lips twitched up into some kind of small smile. "But, thank you."

She dropped her hold on his shoulder and he stepped around her, disappearing into the room behind her; Dean angrily called out something that she couldn't quite pick up, moments before Cas reappeared, carrying a change of clean clothes, his half smile now completely gone, replaced by a scowl across his mouth and sadness in his blue eyes - they seemed darker today, Mary noticed - as he ducked into the bathroom before she could ask any questions, leaving her standing on her landing alone, wondering what on earth had happened to her boys all those years ago.

* * *

 **Sam.**

"What do you think of this?" Gabriel plucked a trilby hat off of the display stand and, with some difficulty, plonked it on Sam's head.

Castiel nodded politely. "Lovely."

"Cassie, you've said that about the last five hats that we've tried on! It's all you've been saying this afternoon! At least say something other than that!"

"Alright." A crease appeared in Cas' brow as his blue eyes studied the hat for a few seconds. "It's very...you?"

Sam snorted, elbowing his bewildered fiancée in the ribs. "Leave him alone, Gabe. If he thinks it's lovely, then it's lovely, okay?"

Gabriel pulled a face. "You're just sucking up to him because you want the better wedding gift."

"Guilty."

This comment made Cas crack a smile - a real smile, Sam was pleased to see, not the polite slight upturn of his lips that he'd worn for the past three days, ever since he arrived at the Winchesters' place - whilst Gabriel simply rolled his eyes and stood on his tiptoes to press a kiss to Sam's cheek. "I'm wise to your games, husband of mine."

"Fiancée."

"Husband _to be_ , then." Gabriel threw them both a wink, catching sight of another display and slipping past them in order to investigate, leaving Sam and Cas to make idle conversation - something that Sam was never really good at and something that Cas didn't seem particularly keen on doing.

"Sorry," Sam said finally, for what was probably the hundredth time since December first.

"It's fine," Cas replied, civilly as always, but the expression on his face was stoic, his previous amusement gone almost immediately after it had broken through. That was okay, though. Sam could live with stoic. What he couldn't live with was the brooding anger that radiated from his older brother on a daily basis.

"How -" He began.

"So -" Cas said simultaneously, causing them both to stop and clear their throats awkwardly, lapsing back into silence.

"How is Pontiac?" Sam asked eventually, distracting himself with the rack of clothing in front of him. Nothing took his fancy all that much.

"Warm," Cas quipped. "Warmer than Lawrence, that's for sure." He paused. "You're a lawyer now." It didn't sound like a question of any sort, more a reassertion of a fact.

"Training to be, yeah. I've only got a few months of law school left."

"I seem to remember you always wanting to do that."

"Yeah." The two of them had been good friends once, often discussing what their future plans were. Maybe not so much anymore, Sam thought. "What was it that you studied at college? Speaking of which, how was college, by the way?"

This appeared to have been the wrong question to ask. The lines across Cas' brow deepened as his face twisted into a scowl. "A waste of my time and money. I chose to study Philosophy, and now look where I am. I'm a freaking _tax accountant_." He spat the words out as of they were a couple of curse words, knocking a few hangers askew as he pretended to look at something on the rack.

Sam blinked at his words, something about them resonating in his memory, dredging up a mental picture that he thought he'd forgotten about: a lazy day in late November, Sam sitting on the floor, Cas and Dean on the couch.

"You look like a tax accountant, Cas," Dean had said, tugging on the sleeves of the trenchcoat, eliciting a glare from the boy next to him. "Aw, c'mon, baby, don't look like that!" His fingers moved from the coat to scrabble at Cas' sides, causing his glower to break instantly, replaced by a fit of giggles as the two of them toppled sideways, sprawled across the couch. Sam had only been thirteen at the time, but he could remember chuckling at the scene in front of him, and then beaming as he watched Dean nuzzle into Cas' neck and kiss the skin there as Cas tried to muffle the sound of his laughter. Sam wondered now if Cas remembered that day and, if he did, if he ever thought about it on occasion. Going by the look on his face, he suspected that the answer was yes.

Sam felt a sudden urge to lay his hand on Castiel's shoulder and apologise, yet again, for something that was not his fault. Instead, he reached into the rack and pulled out the first shirt he saw - bright yellow, with red flowers on - and said in his most convincing voice, "This is nice, isn't it?"

* * *

 **Well, that's all for December 3** **rd** **!**

 **Until December 4th, my little sock puppets... X :)**


	4. December 4th: Crowley, Dean, Castiel

_**December 4th: Crowley, Dean, Castiel**_

 **Crowley.**

Something was wrong today.

Crowley couldn't quite put his finger on what exactly that something _was_ , but it practically _radiated_ drama. He could sense it.

To say that he was friends with Dean Winchester, the squirrel, would have been a lie. He liked to think of them more as satisfied enemies, in a way. They put up with each other when they had to, like the times when Bobby was glaring at them from inside his office during one of the busier days that the garage got to see (they were a rarity, that's for sure), but it was no secret to anyone that they both took great pleasure in hating the other.

Which was really how Crowley's suspicions had first come about. Usually the two of them exchanged insults across the room from the moment that they saw each other at the start of Winchester's shift, but in reply to his usual comment of, "Afternoon there, Squirrel,", all he had gotten was a grunted sound of acknowledgement.

Crowley hadn't actually been sure whether to be hurt by this or not; Winchester _never_ passed up the opportunity to throw insults at him, not once in the three months since his high profile business career went unceremoniously sailing down the river and he had to resort to working in Singer's Garage (because _anything_ was better than the Gas N Sip). Even now, when he was usually belting along to whatever trash the local Lawrence radio station decided to play that afternoon, Squirrel was silent. Well, mostly silent; at odd moments, Crowley caught him grumbling under his breath about something or other. As relieved as he was to not have to listen to the abnormal racket all afternoon for a change, it also left him feeling a little out-of-sorts. What was he supposed to insult Squirrel about, if not the dreadful singing?

"Cat got your tongue?" He asked eventually across the karaoke-free garage, holding the grease-covered spanner in between his fingers in disgust. How on earth was he supposed to use this without getting his clothes covered in dirt? That might not have been a problem for Squirrel, who apparently seemed to thrive when covered in oil stains, but he actually had standards, thank you very much.

"Piss off, you son of a bitch," Dean fired back.

"Wow." Crowley raised an eyebrow. "Now that is just mean. What did I do to deserve that?" Silence. "I must say, Squirrel, I'm surprised. Didn't think you'd be the type to indulge in teenage angst during your mid twenties...or are you just having your mid-life crisis early?"

Dean raised his middle finger at him, as if that was somehow meant to be intimidating enough to silence him. "I wouldn't expect you to understand anythin'."

"Ah. I see." Crowley used this as an excuse to drop the spanner back into the toolbox next to him and folded his arms. "Who is she, then?"

"Huh?"

"Squirrel, as your wiser and more experienced co-worker, I know for a fact that this is classic behaviour from a man who is having relationship troubles. Trust me, I've watched enough of my own past employees break down in front of me for this very same reason, just before I fired them. So, come on, who is she?"

"No one."

"You can't hide anything from me, Squirrel -"

"Dammit, King of Hell, there's no chick!" Dean snapped back. "What part of that is so difficult for you to comprehend?"

"Oh. Oh, I see." Crowley smirked as the scowl grew more ferocious on Winchester's face. "So, it's not a _she_ , in fact, but a _he_. Now, that is _interesting_. I didn't strike you as the type to be a gay man who's out of the closet."

"I'm not!" At the expression on his face, Dean elaborated. "I mean, I'm not gay -"

"Bisexual, then. Whatever. Regardless, what's the issue? Cheating boyfriend? Sour relationship? Bad breakup? Ex back in town?" By the way Winchester's gaze flickered down to the ground, that was as good as a verbal yes. Crowley rolled his eyes. "Squirrel, at the end of any relationship, you have to get back onto the high horse, so to speak. No pansying around, no skulking down here in this dump -" He stopped that sentence pretty quickly, because Bobby was narrowing his eyes in their direction. The man may have owed him a favour from years back, but there was only so much that he would put up with. "You need to show him that you're having the best freaking time of your life without him, and that he should never have given you up."

Dean narrowed his eyes. "Why should I trust your judgement?"

"Fine." Crowley shrugged. "Don't then. Melt away into a puddle of your own tears whilst you watch romantic comedies alone in your room and mourn how much of a better time you know that I'm going to be having." He turned away, hunching over the hood of the car Bobby had assigned to him.

Freaking Squirrel. Always so passive aggressive. Couldn't take any advice, not even if it was plastered to his freckled forehead with holy cement.

Now...

Didn't these vehicles come with some kind of instruction manual?

* * *

 **Dean.**

"I like what you've done with the place."

Jo rolled her eyes, leaning against the bar as she smoothed down the pleated skirt of her fancy dress costume. "Dean, it's the same decorations we use every year. Don't start pretendin' like we've done anythin' special."

Dean shrugged, taking a sip of his beer. "Well, what did you want me to say? " _Sorry, Jo, but it looks shit."_?"

"What was that you were sayin', boy?"

The Winchester almost leapt out of his seat as he whipped his head around fast enough to give him whiplash. Ellen Harvelle was stood behind him, arms folded across her chest, looking unamused.

Jo let out a chuckle. "Mom, he's not being serious. We were just talkin'. Calm down."

"I know." Ellen bumped her shoulder with Dean's, pulling him into a swift, one armed hug as she did so. "But, that better be all you were doin', understand?" She looked between the two of them reproachfully before continuing. "You tell that brother o'yours to get his ass down here as soon as possible, Dean. I haven't given him my blessin' yet."

"He's on his way tonight," Dean replied. "I'll tell him to keep an eye out for you."

Ellen nodded, reaffirming his response. "Good."

Jo's expression morphed into a glower as soon as she'd gone. "Ugh. I don't know what her problem is nowadays."

"What d'you mean?"

"She's always hangin' 'round me nowadays, ya know? Actin' like I'm suddenly some kind of toddler who can't talk to strangers unless she's there with me."

"She's probably just worried."

"Since when did you become the voice of reason in this friendship?"

"I speak from experience. Moms worry all the damn time."

"Yeah, well, I wish they wouldn't," Jo grumbled, pushing away another strand of hair and curling it behind her ear. "How's Castiel Novak these days, then?"

Dean shook his head. "Don't know. Don't particularly care either."

"Have you guys even spoken since he got here?"

"I think I might have told him to piss off this mornin' when I was hung over."

Jo snorted. "Damn. You really do have a way with your man, don't you, Winchester?"

"He's not _my_ man. He's not _my_ anythin'."

 _Not anymore_.

"Whatever you say." Jo shrugged, but her lips curled into a smug smirk that seemed to say "I know everything and you don't". "Didn't you bring a costume for tonight? You're not just sittin' here like a slob until closin' time."

"M'not exactly the festive costume type, am I?"

"Freakin' spoilsport." She reached behind the counter, pulling out a cowboy hat and placing it down on his head before he could protest. "Now, c'mon, if you're not gonna talk 'bout Castiel, you can make yourself useful and help me put up the rest of these decorations before Ash gets back. You're lucky that Mom lets you hang around here all the time."

Dean raised an eyebrow. "Yes, ma'am."

* * *

 **Castiel.**

What was he even _doing_ here?

Cas tapped his fingers against the steering wheel, staring across the well lit parking lot towards the doors of the Roadhouse and the twinkling Christmas lights that surrounded it, illuminating the shadows of people moving around inside the building. The other occupants of the Winchester household had left over four hours ago, waving as they drove away, leaving Cas with the house to himself, free to wander from room to room without having to worry about accidentally running into Dean and making their awkward situation even worse. The peace hadn't lasted, however; the characters in the book he was reading weren't jumping out at him like they usually were, weren't engrossing him with the plot. His mind kept wandering back to the elder Winchester and what he was doing. Was he joining in with the others, making jokes with Sam and Gabriel as they sat at the bar? Was he sitting alone in the corner, drinking beer after beer, watching the festivities in silence? Was he with someone else - a girl he'd met at the garage, with wide eyes and a beautiful smile?

Sighing, he heaved himself out of the car, slamming the door and pulling his trenchcoat tighter around him as he ascended the steps leading up to the Roadhouse, nudging them open with his hip as he crammed his fingers into his pockets in order to keep them warm. The building was bustling with people, filled with the sound of overlapping chatter and cheesy Christmas tracks blaring from the speakers. He was about to turn around and run back to his car as fast was humanly possible, before anyone saw him and attempted to try and make some kind of polite conversation with him, when Mary and John appeared in his line of sight, his arm around her shoulder whilst she nuzzled into his side.

"Cas!" Her smile grew wider when she saw him, holding out a hand towards him, trying to coax him closer. "How lovely, you decided to come along, sweetheart! John and I are off home now that it's getting close to midnight, but Gabe and Sammy are still around. Here, love, get yourself something to drink, on us -"

"No, no, I couldn't -"

"Don't argue with her, boy." John pressed a handful of bills into his pocket, ignoring Cas' protests. "You're only fightin' a losin' battle." Mary elbowed him in the side, grinning, and he nodded towards her. "See what I mean?"

Cas chuckled mirthfully at the happy couple as they left the bar, shaking his head a little as he thought to himself, moving across the room to where his brother and his fiancée were sitting by the counter. Well, not exactly - it was more where Sam was sitting and where Gabriel was trying and failing to climb into his lap after drinking one too many beers.

"I thought tonight was supposed to be a family friendly event, Gabriel," Cas remarked dryly.

Gabriel cast an exasperated look in his younger brother's direction. "Ah. I knew that you'd show up eventually, Cassie. In case you hadn't noticed, it's nearly midnight. All the kids have gone home; all bets are off right now. Isn't that right, Samsquatch?" He made another advance towards Sam, who gave him another playful shove.

"Hey!" A young blonde glided into view, giving Gabriel a whack on the back of the head. "Just 'cause the kids have gone home, doesn't mean I wanna bear witness to all that." She rolled her eyes, suddenly doing a double take when she noticed who was on the bar stool in front of her. "Holy sh - Are you - You're Castiel Novak, right?"

"Hello," he greeted, brow creasing a little. "I'm sorry, I don't think I remember you."

"It's Jo," the blonde prompted. "Jo Harvelle. My mom Ellen runs this place."

"As in the Jo Harvelle that I went to high school with?"

"The one and only." Jo beamed at him, rooting under the counter for something before leaning over her shoulder to yell something. "Ash! We need more whiskey out here!" She turned back to the blue eyed man in front of him. "I've been waitin' for you to drop by. Wanted to catch up." She slid a glass across the table. "On the house. Call it a Welcome Back gift."

"Thank you." He took an experimental sip, and tried not to recoil at the bitter taste. "How have things been around here?"

"Great, great. Actually -" Jo looked distracted. "Would you excuse me for a minute? Thanks." She stepped out from behind the bar, throwing a casual arm around a brunette woman as she called off into the distance. "Dean! Dean, get your ass over here!" Cas watched in curiosity as the elder Winchester materialised seemingly out of no where, a bottle of something in his right hand. "This is Lisa - that friend of mine I was tellin' you 'bout?"

The younger Novak cast his eyes away again, swirling the liquid in his glass. Suddenly the alcohol didn't seem so appealing; his stomach felt odd, his insides twisting and churning uncomfortably.

"Cas?" Sam had noticed the look on his face and laid a hand on his shoulder, making him start. "Cas, you okay?"

" - Sorry 'bout that." Jo reappeared in front of them. "Just some business I needed to take care off with my dumbass best friend...Hey, what's up with Castiel?"

Cas sucked in a breath. "Sorry," he mumbled. "I don't think I'm feeling too well. Excuse me." He swiftly rose from his seat, pushing the collection of bills John had given him across the counter. "Thank you for the drink." With that, he turned on his heel and strode from the bar, slamming the door behind him, just as the clock on the far wall chimed midnight.

* * *

 **Well, that's it for December 4** **th** **!**

 **Until December 5** **th** **, my little sock puppets... xx  
**


	5. December 5th: Gabriel, Jimmy, Castiel

_**December 5th: Gabriel, Jimmy, Castiel**_

 **Gabriel.**

Gabriel stared at the door his little brother had just disappeared through, before he turned around again to face Jo, a scowl forming on his face. "Hey! What the hell did you do?"

The blonde girl looked dumbfounded, her eyes still watching the stool where Cas had been sitting moments earlier until she processed Gabriel's words. "Whoa, whoa, I never did anythin'! I was gone for, like, two seconds and then he wasn't feelin' well, so he just left!"

Gabriel let out a groan. Honestly. People these days. "Christ, Jo! " _Not feeling well_ " is Cassie's way of saying " _Something's_ _up_ _and I need to get out of here before I make a scene, so don't ask me what's wrong_ _because I don't want to, and therefore will not, tell you_."."

"And I'm supposed to know this... _how_ , exactly? C'mon, I barely knew the guy in high school and I haven't seen him for seven years! Forgive me if I'm not the Castiel Novak expert right now. Back me up on this one, Sam!" She looked expectantly towards the younger Winchester, but Sam didn't appear to be concentrating on the conversation going on beside him. He was far more interested in something else, further along the bar.

"Say," he said suddenly, frowning in concentration. "Who's that Dean's talking to?"

Both Gabriel and Jo followed his gaze, landing on the elder Winchester and the slim brunette he had his arm tucked around. Jo exhaled loudly. "Lisa Braeden. She was my best friend in high school. She's been complainin' 'bout how lonely she is, y'know, as a single mom an' all that, so I put her in touch with Dean."

Gabriel spluttered around his mouthful of beer. "You put - _What the hell did you do that for?_ "

Great. How on earth was he supposed to get Cassie to understand that Dean was still in love with him with _this_ going on?

 _Thanks_ _for that_ _, Harvelle_ , he thought bitterly. _Thanks a freaking bunch._

"Hey!" She glared at him. "Don't you start somethin' with me! How was I supposed to know that you two were still rootin' for those two chuckleheads to get back together or somethin'?"

Was she being serious? Was she _actually_ being serious?

It was at times like these that Gabriel really didn't like being one of the two fruit loops that lived in a world of basic and standard maple loops. (Sam was obviously the other one; fruit loops were destined to be together forever, after all.)

"How were you - How could you not see how in love with each other they still are?" Gabriel demanded. "Honestly!"

"Well, _sorry_! I only wanted to shove Dean out of the heartbroken funk he's been in for the last God knows how long. Y'know, trying to be what's called a good friend -"

"Hey! Guys!" She was cut off rather suddenly by the other Novak twin stumbling drunkenly into view, supported by a concerned Amelia who was trying to wrestle his drink away from him. "Where's Cassie? I thought he was just here."

"He was," Gabriel replied witheringly. "Until _someone_ , mentioning no name -"

"Hey!" Jo pulled a face. "When this whole sorry break-up mess began, I don't remember you having to listen to the hours upon hours of his sorry ass wailin' 'bout how he don't know how he's gonna cope without his _bumblebee_." She rolled her eyes at the mention of Dean's old pet name for Cas, the one that he'd used for most of the time that they'd been dating.

"No, but _we_ have had to put up with his angst-ridden ass moping around the house for the past seven years!" Gabriel snapped.

Clearly not satisfied with the amount of attention he was receiving, Jimmy cleared his throat, flailing a hand through the air to silence them, almost clipping Sam in the shoulder. "Yeah, yeah, whatever. Pipe down, Gabe, 'cause I've been doin' some thinking, okay, and I got an idea. It's a really good one too."

"Jimmy..." Gabriel folded his arms and narrowed his eyes, the concerned big brother that he often didn't show beginning to emerge. "How much have you had to drink tonight - or rather, this morning?"

"Shh..." Jimmy waved a hand towards him again. "Don't ask for answers that you can't handle, brother. But, enough 'bout me. _Wait_ 'till you hear my idea."

* * *

 **Jimmy.**

"Wait, wait, wait..." Sam held up his hand in order to speak. " _That's_ your great plan? _Really_?"

"Yup!" Jimmy agreed cheerfully, pleased with his efforts. It wasn't often that he came up with good ideas like this when he was drunk; usually his drunken plans involved trying to do a handstand whilst riding a cow or something.

Wait, wait...could _cows_ do handstands?

Cows were clever. Cows could do anything.

Hehe, cows.

"So, what?" Jo looked skeptical. "You're gonna pull a Shakespeare on 'em and accidentally on purpose tell Cas and Dean that they still love each other?"

"You been reading _Much Ado About Nothing_ again, Jim-Bob?" Gabriel asked, causing the others to send curious gazes in his direction. "What?" He looked put out by the reaction. "I know Shakespeare too."

"Whatever! The point is, it's _genius_! Don't you people get it?" Honestly. These people. Couldn't they see what was right in front of them? What was the world coming to? (Actually, Jimmy didn't particularly want to know the answer to that, because the world was clearly going to rot from where he was standing). "Cassie and Dean are so awkward that they'll start talkin' to each other again. And we all know where that leads."

"I wouldn't say _all_ of us know where that leads," Gabriel replied.

Jimmy sent him a deadpan expression, before exhaling melodramatically for effect. "Sooner or later, one of them is going to break. One of them is going to cave in and confess to the other one about how they really feel. And, then, boom. Sweet lovin'." He mimed brushing imaginary specks of dust from his hands. "Like I said, it's genius, really." Goddamit, it really was. He should get drunk more often if it led to amazing ideas like this coming out of his brain.

Speaking of which, _brain_ was such a stupid word. Who on earth came up with that? Who thought it would be fun to call it a _brain_? Why not... _head controller_ , or something like that?

Yeah, that made _much_ more sense.

He was on a _roll_ tonight.

Hehe.

"Jimmy!" Sam's hand was suddenly waving in front of his face.

"Huh?" He blinked.

Oh, right. Someone had been speaking the entire time.

"I said, do you really think that this will work?"

"Absolutely!" Jimmy slapped him on the back encouragingly, stumbling slightly as he did so, causing Sam to wince and Gabriel to glare protectively, wrinkling up his nose as he reached out an arm towards his fiancée. "Wow, Gabriel. You look like a pug when you pull that face." There was a momentary pause before the younger Novak descended into giggles, gesturing to Jo for another beer.

Man, not only was he on a roll, he was freaking hilarious.

"Jimmy -" Amelia still had her arm around him "- I think that's enough beer for now. Gabriel looks ready to shoot you."

"Don't think I won't," Gabriel scowled. "The only reason I'm not doing it now is because he's my little brother."

"I knew that you loved me really," Jimmy smirked.

"Yeah, yeah, Jim-Bob. Don't push your luck."

* * *

 **Castiel.**

The house had been shrouded in darkness when Cas had eventually arrived home from the disaster that had been his brief stint at the Roadhouse. He'd burrowed under his duvet and curled up on Dean's bedroom floor almost as soon as he'd shut the front door behind him, but that had been half an hour ago, and here he was, still awake, staring at the ceiling, unable to get comfortable enough to drift off. His stomach was still churning as he thought about Dean and that other girl, Lisa (he vaguely remembered her from high school; she'd been on the chess team with him one year, if he recalled correctly, and they'd spoken a couple of times, a few mere greetings as they'd passed each other in the hallways). It had made him feel... _odd_ , to say the least. His face had flushed, his heart rate had gone up, and suddenly he had wanted to be as far away from Dean as he possibly could be (even more so than he had done before).

He'd seriously considered making a break for it altogether and driving back to Pontiac right there and then, but then, of course, he would have had to come back in the New Year for Jimmy and Amelia anyway, and it would have been even more awkward than it was already. He could almost see Dean, watching him from the landing, smirking at the fact that Castiel Novak had basically run away from him. He couldn't let him have that victory.

Sighing, he rolled over onto his side, facing the wall, and squeezed his eyes tight shut, trying to will himself to fall asleep and to think about anything and everything that wasn't freaking Dean Winchester.

* * *

 **Well, that's all for December 5** **th** **! Until December 6** **th** **, my little sock puppets... x**


	6. December 6th: Dean, Castiel, Sam

_**December 6th: Dean, Castiel, Sam**_

 **Dean.**

See, this - _this_ _,_ right here - was why he should never listen to Jo Harvelle.

Dean dragged a hand across his eyes as he pulled himself up out of bed, wincing at the stiffness in his muscles. He'd woken up yesterday mid-morning with a girl named Lisa - Jo's friend that he vaguely remembered from high school or something - with absolutely no recollection of how he had actually gotten there, resulting in a rather awkward Saturday lunch with Lisa and her son Ben, and then an equally awkward phone conversation with Bobby to explain why exactly he hadn't turned up for the extra shifts that he had agreed to do. He'd slipped away as soon as was polite to with the tentative promise of a phone call, careful to avoid the dog that belonged to the next door neighbours, disappearing into his room almost immediately after stepping through his own front door, by-passing Gabriel and Sam who were muttering together in the kitchen about something or other that he couldn't be bothered to eavesdrop in on, collapsing down onto the bed in order to sleep off his hangover (at least he wasn't alone in the fact that a few of the others were also hung over and recovering, he thought, muffling his face into the pillow for the second time that week), not even reacting when Cas turned in for the night and then left again in the morning. Sometimes, Dean found himself wondering what the little nerdy guy found to do all day; the few times he'd actually remained in the same room as him for long enough, he was curled up with some seven hundred page novel by some author that Dean had never heard of.

He let out a sigh as he stumbled his way across the landing towards the small bathroom, which, thank Christ, was currently unoccupied; he locked the door behind him, turning the faucet on and splashing his face with cold water to try and clear the sleep from his eyes, moving back to lean against the sink a few seconds later, listening to the sound of his own breathing and the soft noises coming from outside of the door as people padded across the landing.

"...just feel bad for _him_ ," Sam was saying. Dean shut off the water so that he could hear better. "I mean, I've been in that situation before, man. Good God, I've been there. And he's not exactly that advanced in the knowledge of how to handle relationships. That's gotta be tough."

"I agree," Gabriel piped up. They sounded as if they were hovering outside of the bathroom door, leaning up against the wall. Maybe they didn't realise that it was occupied. They did tend to become rather distracted around each other, that much was for sure. Dean had, on many occasions, had to repeat questions at least three times before Sammy got his head out of the Gabriel-scented clouds in order to hear what he was actually saying. "My brother has had the grand total of three significant others: Meg Masters, Hannah something-or-other...Shirley? Something like that, and your brother. Considering the latter is involved in this little dilemma, the others aren't all that much to go on."

"I doubt that this is in any way easy for him."

"Is Deano easy to love?" Gabriel snorted. Despite the fact that he was still trying to process what the hell he was overhearing, Dean glowered at this comment and flipped him off, forgetting for a moment that his soon-to-be brother-in-law couldn't see him through the door.

"To be honest -" Sam sounded like he was shrugging " - I kind of knew that he was still in love with Dean. If he was really over it, he probably would have kept in touch."

 _...What._

"I knew it even before he told me. It was pretty freaking obvious, after all. I mean, come on, the way his eyes follow that brother of yours around the room? He'll deny it until kingdom come, but he'll leap in front of that dumb bastard and take a hit for him, no questions needed."

"What about Dean, though? You think he's cottoned on to it?"

"Pfft," Gabriel snorted. "Who knows what that ass has managed to absorb when he's not drinking himself to sleep every night to escape his lingering feelings for my little brother."

"He doesn't drink himself to sleep every night," Sam replied, sibling loyalty in his voice.

 _That's right, Sammy. You tell him._

"Whatever. I was close enough. I'm sure if Cassie didn't have such a high tolerance for alcohol he'd be doing the same. Especially now that he's let it slip about, y'know, his little problem. Although, thinking about it, maybe problem isn't the right adjective. After all, it's not like Deano's ever gonna find out about this. I was sworn to secrecy."

"So, why exactly are you telling me?"

"Because you're my fiancée now, Sam. I can't have the foundation of our married life together built on a pack of lies."

"Remind me, how does your brother still having a thing for my brother affect our married life?"

"We'll all be family soon, Samwich. Even more so than we are already." Gabriel was probably nodding at this point, trying to sound like he knew what the hell he was on about (Dean would willingly choose cake over pie before that day arrived). "Family doesn't lie to each other."

"You sound like Bobby," Sam chuckled. " _Family don't end with blood, boy._ "

"The man's wise, Sam. You should listen to him." There was a momentary pause. "Now, what was it that you came up here to get?"

" _Pulp Fiction_. Jimmy's insisting that we watch it."

"Not really what you'd call a Christmas movie, is it?"

"Yeah, well, we're not really what you would call a Christmas-y family, are we?"

"Eh. Fair enough." Gabriel hummed in agreement as their footsteps began to fade away from outside the bathroom, heading towards Sam's room, leaving Dean slumped against the door, his ear pressed up to it, not entirely sure how to process what the hell he had just heard.

* * *

 **Castiel.**

" _I'm_ _,_ _I'm so in love with you_ _._ " Cas let the teabag sit idly in the mug on the counter in front of him, humming quietly to himself as he did so. " _Whatever you want to do_ _..._ _Is all right with me._ " Why on earth his twin brother wanted to watch _Pulp Fiction_ , of all things, Cas had no idea. It wasn't exactly the typical Christmas movie - but, then again, this wasn't the typical Christmas, and so Jimmy had insisted that he hang out with them before he had been sent into the kitchen to retrieve tea for everyone else. At any other time, Cas would have complained, but with Dean asleep in bed upstairs despite it being mid-morning, and no where else to really go considering the amount of rain that had ascended on Lawrence in the last hour or so, his options for activities to occupy himself were limited.

"' _Cause you..._ " He continued under his breath, loading the last mug onto the nearby tray and tossing the teabag in the garbage can on his way out of the door, " _..._ _make me feel so brand new...And I... want to spend my life with you..._ " He paused at the threshhold of the living room, listening to the sound of Jimmy and Amelia laughing amongst themselves as a piece of popcorn went sailing through the air (no doubt from his twin brother), a smile forming on his face. Despite the mess he had made of his own relationships, Jimmy had done surprisingly well for himself; after all, Jimmy was the same one who had eaten dirt during ninth grade on a dare. Supposedly being a mature, responsible adult now couldn't erase that memory.

"Should I invite Dean?" Amelia was saying, now that the general merriment had died down. "I know he came in pretty late yesterday and hasn't left since, but he might appreciate the company."

"Nah," Jimmy replied, probably shrugging. "I wouldn't if I were you. Especially when he's like this. He's hungover like a dog after getting it on with Lisa Braeden or whatever her name was. Besides, I don't really want to listen to him grumbling about how hot my brother is. That's kind of uncomfortable when you're one of a set of twins."

 _Grumbling about what?_

"I can imagine," Amelia snorted. "So, what did he actually say to you guys?"

"I think he was already more than a little drunk at the time when we ran into him at the Roadhouse before he went off with that Lisa chick - Well, we were _all_ more than a little drunk that night -"

"No, Jimmy. I do believe that was just _you_. Not all of us tried to attack the local farmyard on the way home and then had to lie in bed nearly all of yesterday to try and sleep off all that alcohol."

"Okay, maybe that one was just me. But, anyway, back on the topic of Dean; that Lisa girl was just as drunk as he was, if not more, and was trying to drag him back to hers, but he kept going on and on about Cas and _he's my little bumblebee, yeah?_ It was all very angsty and brooding - and I seem to remember something about cows too, but that might have been my contribution to the conversation - but I can't remember the exact wording he used, not just because his voice was so slurred. Good thing I was sworn to secrecy."

"So, why are you telling me?"

"I can't exactly talk to Cassie about this stuff, can I? I'm pretty sure it would not go down well with anyone if I told him. " _Hey there, bro, that douche that broke your heart seven years ago and caused you to break down in my arms in the middle of the street still has a massive crush on you and would probably want nothing more than to have sex with you the next time that you guys are alone in a room together -_ " He stopped suddenly. A loud crash had emitted from somewhere. "Cassie?"

Cas blinked as his twin brother's face appeared in front of his. He'd dropped the tray in shock, he realised, looking down at the puddle of tea that had formed at his feet along with several chipped mugs, his empty hands still hovering in mid air, holding the same position they had been before.

"Cas?" Jimmy was watching him, both in confusion and concern. "Are you okay?"

It took him a moment to reply. "Fine. Really...really fine. Just being clumsy." He quickly bent down to pick up the ceramic mugs and gather them on the sopping wet tray, trying to hide his face from view in order to not give away the expressions that were threatening to swarm and cloud his face.

* * *

 **Sam.**

"Did it work?"

Jimmy snorted quietly, glancing back over his shoulder to make sure that they hadn't been followed. "Of course it worked! He dropped the freaking tea tray, for crying out loud. And he hasn't focused on the movie at all since it started. It's quite amusing, really. How did you guys get on?"

Sam shrugged, leaning against the kitchen counter, wondering whether it was appropriate for him to be feeling some kind of Disney villain glee right now. "I assume that he heard us. Gabe and I were both yelling loud enough for him to overhear." He paused. "Now what?"

"Now, we wait."

"Wait for what?"

Jimmy looked at him as if it was obvious. "Wait for the perfect moments to start inputting our influence, of course."

"Of course," Sam repeated, eyes rolling heavenwards "Why didn't I think of that?"

* * *

 **Well, that's all for December 6** **th** **!**

 **Until December 7** **th** **, my little sock puppets... X :)**


	7. December 7th: Bobby, Dean, Castiel, Sam

**December 7th: Bobby, Dean, Castiel, Sam**

 **Bobby.**

"Okay, boy. What is it?"

"Hm?" Dean seemed to snap out of his daydream, inclining his head in the direction of his boss. "What d'you say?"

Bobby let out an infuriated huff. As if it wasn't bad enough having to deal with Crowley and his total incompetence when it came to mechanics and all that it entailed. He didn't need to deal with this too. "You've been mopin' 'round here all afternoon, fixin' and then demolishin' the same damn car over and over again. If you can't work properly, I'm gonna have to send you home for the rest o'the day until you're back on top o'things."

Dean ducked his head, looking a little embarrassed. "Sorry. Just got a lot to think 'bout right now, y'know?"

"I noticed. And I understand that. But this is the workin' world, son. You gotta be focused if you wanna get on."

"Yes, sir."

Bobby snorted. "Alright. Enough of that nonsense." He leaned over to fondly clap Dean on the back of the head as he returned to his work, discarding the spanner in his hand and delving into the toolbox beside him for another piece of equipment.

Crowley was leaning against the desk when he got back into the office, arms folded, eyebrow raised. "What's up with the squirrel?"

"God knows." Bobby cast a look behind him at the employee, who was now hurrying in order to make up for the time he'd lost whilst gazing out of the window at nothing in particular. "But, I tell ya, he ain't been the same since that Novak kid came back to town last week."

"As in _Castiel_ Novak?"

"Uh hu."

Crowley smirked gleefully. "Squirrel's ex...is Castiel Novak? Hah! Oh, I would have paid good money to see that! How in the hell did Dean Winchester, Squirrel, end up with a Novak?"

Bobby sent him a sideways glare at his flippancy. "Those boys were friends for years. Joined at the damn hip for nearly two decades. Anyone with a inch of common sense could see how they felt 'bout each other."

Crowley scoffed wordlessly. "I'm amazed Squirrel was allowed within three metres of the boy. I had dinner with the father of the Novak clan one time at their old place. Kids were paraded around the room once and then sent to be put to bed. I didn't know whether to laugh or feel sorry for them. I can't imagine that uptight giraffe was too impressed when he saw who his precious prodigy had ended up with. Still -" He brushed imaginary dirt from his hands, as if to free them of the entire matter "- no use talking about the past today, eh, Singer? Squirrel and Novak seem to have a mutual hate for each other nowadays, so it all worked out in the end."

"Not for Dean." Bobby nodded his head towards the boy in question, a note of sadness in his voice when he thought about the misery that had radiated from the Winchester when Castiel had packed up his things into the trunk of his old car and put the town of the Lawrence behind him. Dean could hold a grudge like no one else.

Crowley shook his head. "I gave Squirrel advice, and he wouldn't take it. It's his own fault if he can't let go of the past." He held his hands up, in some kind of mock surrender, sidling towards the door. "Only so much a man can do after all."

"Suppose so." Bobby hummed in agreement, lost in thought for a moment before snapping to attention. "Hey! Where d'you think you're sneakin' off to? I still want a word with you 'bout Azael's car."

"Oh, come on, I barely touched the thing!"

"You destroyed the gearbox!"

* * *

 **Dean.**

Dean bundled his jacket tighter around him as he slid into the Impala, quickly starting the engine in order to get on the move. The sooner he was on the road, the sooner he could get home, out of the pouring rain that had started twenty four hours beforehand and hadn't let up since then. What a miserable way to ease into the festive season. But it also reflected Dean's mood; he hadn't forgotten what he had overheard Gabriel saying to Sam yesterday. In fact, he'd spent the rest of that day, and almost all night, thinking about it, what that meant for him. Because, quite frankly, his situation would be much easier if Castiel hated his guts, hated him with a burning passion, like he was expected to. Then Dean could just mutually hate him back, and everything would be fine.

Of course, he should have known something like this would happen. Cas didn't hate people. He thoroughly disliked people, but he never seemed to actually hate anyone, not even Dean, not even after everything they had said to each other when they broke up.

Dean let out a sigh as the Impala pulled out onto the road, swerving around the street corner. Not for the first time, he wished that Cas could hurry up and go back to Illinois. Go back and take all of his feelings, and big blue puppy dog eyes, and ability to make people's heartbeats go crazy in their chests with him, because Dean didn't need it. Didn't need it at all.

 _Who are you trying to convince?_ A little voice that sounded suspiciously like Sam said in the back of his head (probably accompanied by one of Sam's bitchfaces).

"Shut up, Sammy," he said aloud to the empty passenger seat beside him. Somewhere in the depths of his mind, he swore he heard Figment-Sam laughing as he turned another corner - and then almost groaned aloud as he did so.

Castiel was squatting in the doorway of the nearby bookshop, just a little up the street, his purchase clutched to his chest in a vain attempt to keep it dry. His clothes were already soaked through, droplets of rain leaking out of his dark mop of hair and dribbling down his face.

Three days ago, Dean would have thoroughly considered driving past - if not, have actually done it - grinning smugly to himself as he did so, but today Gabriel's words echoed in his ears.

Cas still liked him. As in, _lik_ e liked him.

And, maybe because of that, he couldn't just drive past and leave him.

Except he wasn't supposed to do things like this. He wasn't supposed to like Cas - not that he did or anything (whatever Figment-Sam was trying to imply), but still. He wasn't supposed to like his ex. He was supposed to go off and have the best time of his freaking life without him.

And yet something in him, some spark buried and forgotten, would not allow him to drive away.

He drew up beside the sidewalk, close to where Cas was hovering, and across the seat to roll down the passenger window. "Hey! Castiel!"

Cas practically jumped out of his skin, before his eyes sought out who was sitting in the car a few metres away. "Dean?"

"You need a ride home or somethin'?"

Cas paused, as if trying to judge whether or not he was being serious, before seeing nothing suspicious behind Dean's motives and dashing out of his spot towards the Impala, keen to get out of the foul weather; Dean unlocked the door and returned to the driving seat in order to let the bedraggled-looking man climb in.

"Thank you, Dean," Cas said gruffly, shutting the door behind him, pushing a clump of soaking wet hair from his eyes.

"No problem," Dean muttered in reply as he steered the car back onto the main road. "No freakin' problem."

* * *

 **Castiel.**

Cas kept his eyes on the road straight up ahead as the Impala drove on, tracking the movement of the raindrops that trickled down the windshield. He'd only braved going out in the rain in the first place (under the notion that it had to stop sooner or later) to escape Sam and Gabriel, who were starting to become to couple-y for their own good, when the heavens had opened above him, leaving him stranded in the doorway of the bookstore, facing a walk home in the downpour.

Until Dean had offered him a ride. Dean Winchester, who hated his guts with a passion, offered him a ride.

Except...

Well, according to Jimmy, he _didn't_ hate his guts, did he?

"So," Dean said suddenly, breaking the silence between them. "How, uh, how's it goin'?"

"Um...fine. Thank you." Cas shifted in his seat, the atmosphere awkward. "How, uh, how are you?"

"Fine."

"Well, good."

"Yeah. Good."

They lapsed back into awkward silence. Cas toyed with the plastic bag sitting in his lap, the action seeming to catch Dean's attention.

"What you, er, What you readin' now?"

"Just _A Tale of Two Cities_ again. I thought it was worth a re-read."

"Dickens, huh? You like the classics, then?"

Cas sent him a look out of the corner of his eye. "I've always liked the classics."

Dean didn't meet his gaze. " . Yeah. 'Course you have." He cleared his throat. "They, um, any of them any...y'know, good?" Cas noticed him wincing to himself as the words left his mouth.

 _Is he trying to flirt with me?_

"Most of them, yes. You should read some of them sometime."

"Oh. Yeah. I, um, I will."

That appeared to be the end of the conversation for now. The rest of the journey was taken in awkward silence, Cas not sure where he should look, Dean clearing his throat at odd intervals in order to dislodge some of the tension (not that it was working).

"Thank you for the ride back," Cas said eventually, when they had pulled up outside the Winchester home. "I appreciate it."

"Oh..." Dean scratched the back of his neck, looking almost sheepish, a habit he tended to do when he was uncomfortable. Cas remembered that expression well; he'd worn it just mere moments before they had kissed for the first time. "Don't worry 'bout it." There was another pause. "Better get inside, though. Rainin' like hell out here."

"It is," Cas agreed. "Although not quite as much as earlier." He unlocked the passenger door and got out, hurrying up the garden path with Dean a few paces behind him, both of them in a rush to escape the cold and damp conditions.

Gabriel and Amelia were seated in the kitchen making Christmas decorations when they arrived indoors, Cas shrugging his sopping trenchcoat from his shoulders.

"Cassie!" Gabriel greeted with a smile on his face. "And...Dean!" He exchanged a look with Amelia, who had laid her scissors down in order to observe what was going on. "I didn't expect to see you guys...y'know, together." He held up his two index fingers and moved them together.

"Yeah, well..." Dean reached to scratch the back of his neck again. He was uncomfortable again. "S'just a random good deed, isn't it?"

"Random sounds about right," Gabriel snorted.

"But good sounds about right too," Cas cut in.

Dean shuffled again. "Well...good," he mumbled, trying and failing to inconspicuously back out of the room.

Cas slid his gaze to the floor as Amelia spoke up. "What's up with Dean today?"

"Who knows," the younger Novak replied, more to himself than to her. "Who knows."

* * *

 **Sam.**

"Aw!" Sam grinned and tried to clap (it was very hard to do one handed), pinning another snowflake to the living room ceiling. "That's actually so sweet. I didn't think Dean had it in him."

"I didn't want to say "I told you so"," Jimmy chimed in, "but, I told you so."

"Yeah, yeah." Gabriel gave his brother a playful poke in the ribs. "I still stick by what I said earlier and think that we should just shove them in the closet again like you did last time."

"Not yet!" Jimmy elbowed him. "Gabe, DeanCas, it's like a pie. You don't just throw the objects in a bowl however you like and hope for the best! You have to let it simmer in the oven first before it's ready to eat!"

"What the hell is _DeanCas_?"

"It's their name." Jimmy glanced amongst the three others in the room. "You know, like their couple name. Dean plus Cas is DeanCas."

"Why not CasDean?" Gabriel offered. "Castiel comes first in the alphabet."

"Surely it would be Caean, though?" Amelia jumped in. "If you want to really mash their names together."

"No, no, I got it!" The older Novak held up his hands. "How about... _Destiel_?"

Jimmy nodded, making a noise of approval as he did so. "I like it."

"Me too. It's kind of sweet."

"Wait, wait..." Sam's brow was creased slightly. "Shouldn't it be, like, _Deastiel_? Wouldn't that make more sense?"

"Samwich, since when has Deano and Cassie's relationship ever made any sort of sense?"

"Suppose not." The younger Winchester gave a shrug. Gabriel had a point there. "Well, then. Destiel it is."

* * *

 **I'm sorry for the lack of update yesterday! We went on a university trip, and my brain was dead by the time I got home. So, there'll be two chapters today! The next one will be posted when I get home from school. I'll see you then, my little sock puppets. :)**


	8. December 8th: Dean, Castiel, Jimmy

_**So the getting back on track the other day and also yesterday like I had planned clearly died a painful death when I realised how much homework I still had left. Luckily, there's only a week or so left of school, so I should get back on track in the next week now that the work load has eased up a little bit...*famous last words*...**_

* * *

 _ **December 8th: Dean, Castiel, Jimmy**_

 **Dean.**

The sound of stumbled footsteps and muffled cursing pulled Dean out of his sleep.

"What the -?" He lifted his head from the pillow to squint at the figure a few metres away from his bed. "Cas? What are you -?"

"I'm sorry." Castiel stood in the centre of the room, a jacket only half put on, an apologetic expression covering his face. "I didn't mean to wake you. I know it's your day off and everything -"

"Nah..." Dean stifled a yawn as he mumbled a reply. "S'good. Where you goin' so early?"

"Shopping." Cas gave a shrug. "It's come to my attention that I haven't actually bought anyone anything for Christmas yet, and there's only a couple of weeks to go until the big day, so I thought I'd better get a move on."

Oh, right. Christmas shopping. Dammit, he knew that he'd forgotten something.

He rolled his eyes and snuggled down a little further into the nest of blankets that he'd managed to create during the night. "Don't look so worried, Cas. I don't do my shoppin' until the last few days before Christmas. There's always somethin'."

"I suppose." Cas managed to get his other arm into the tan jacket, almost a shorter version of his trenchcoat. "But I still have no idea what I'm going to buy for people." He paused for a moment, obviously thinking something through. "Dean?"

"Hm?"

"This may sound a little out of the blue, but...would you like to come with me?" He let out a heavy exhale at the end of his question. "It's just, I haven't got any idea of what to get Sam and Gabriel, and I know that you haven't got anything either, so I thought, maybe, we could...help each other out? Sorry. I know you've only just woken up, but -"

"Whoa, Cas, man, calm down." Castiel was speaking way too quickly for this early hour of the morning. Dean pulled himself into a sitting position, watching the other man chew on his lip as he waited for a response.

"You don't have to," he said after a moment. "It was just an idea - I don't want you to feel obligated, like you have to spend time with me -"

"What if I want to spend time with you?" Dean asked before his brain-to-mouth filter had had the appropriate amount of time to process his answer.

Cas went a startling shade of red, his gaze suddenly very fascinated by the beer stain that still lingered on the grubby bedroom carpet. Now Dean understood what Sam had meant when he told Gabriel that he felt bad for the younger Novak. Cas clearly had no idea how to be subtle about his school-boy crush.

"Then...that would be lovely."

"Right." Dean cleared his throat. "I'll just...y'know, go take a shower and everythin' -"

Cas nodded, rather too enthusiastically for the situation. "Yes. Shower. You should...You should do that. Showers are good. Go have - Go have a shower." He made an odd shoo-ing gesture with his right hand, before letting out another loud gust of air and all but sprinting from the room as fast as was polite. Dean watched him go and then sighed, hauling himself up and out of bed, padding quietly across the landing and into the bathroom, locking the door behind him. If he hadn't been sold before about Cas' supposedly obvious crush on him, he was definitely sure of it now. Sam and Gabriel hadn't been generous enough with their description; it wasn't just obvious, it was painfully obvious. Dean had had several relationships in his life, and not once had he had an ex react the way Cas had done. They were mostly angered by the sight of him - like he had been three days; they weren't exactly the perfect candidates for a day of Christmas shopping.

But, then again, this was _Cas_. When was Cas _not_ anything but normal? Dean could remember countless times when his best friend had done things that others had raised eyebrows at and he had just accepted it, put it down as one of Cas' little quirks. Arguing with yourself out loud in public? Losing said argument against yourself? They were just Cas things. It only made sense that this sort of weirdness would transfer over to situations like this, before Jimmy was given another opportunity to shove them into a closet and not let them out until they had made out for at least ten minutes (it had turned out to be longer than ten minutes, Dean found out later, when Jimmy had informed him that they'd been in there so long that he was tempted to venture into the closet himself to see if they hadn't passed out in there). Cas was a little hopeless when it came to relationships. Not that he was any better himself, but at least he could tell one type of feeling from another.

Well, most of the time.

Aforementioned Cas was wandering aimlessly around the kitchen by the time that Dean eventually got out of the shower, again seemingly talking to himself, tugging his hat down further over his head until it was almost covering his eyes.

" _Hey,_ " he was muttering, his back to the new addition to the room. " _I was wondering if we could chat -_ Oh, God, no, no, not chat. Um, _Hey, Dean I have something that we need to discuss - talk about - delve in to...Hey, Dean, I don't know if you realise that I -_ Ugh!" He cut himself off with a frustrated groan, letting his forehead thump against the refrigerator. "For God's sake, Castiel, you're a _grown man now_."

Dean wasn't sure whether or not he should just tiptoe away and try his entrance again. "Uh, Cas? What are you doin'?"

Cas let out a startled yelp, whirling around to face him. "Nothing!" He said, too quickly to sound any way convincing. "Just...thinking. Are you, um, are you ready to go yet?" He didn't wait for Dean to give an answer; instead, he hurried towards the front door, eager to get out into the early morning in order to avoid looking the older Winchester in the eye.

This was going to be a long day.

* * *

 **Castiel.**

Was there actually a limit for how many times he could embarrass himself in one day?

Cas wrapped his fingers around his cup of coffee, trying to warm them through the flimsy paper. Clearly he was trying to set some kind of new personal record. As if Dean's apparent crush on him wasn't making things awkward enough.

"It's, er, it's starting to snow."

"Wha'?" Dean looked up from the bacon roll that he was currently devouring, following the younger Novak's gaze out of the window of the small diner that they'd relocated to after a couple of hours of unsuccessful shopping. Even at this early hour, the streets had begun to fill with people, all of whom were now rushing to get out of the way of the flakes that were now beginning to tumble from the overcast sky above. "Oh. Yeah. Guess it is." He dropped the last chunk of bread back onto the plate in front of him, brushing crumbs from his fingertips. "First snowfall o'the year. It's early."

Cas nodded. "Compared to how many days we used to wait for it, yes, it is."

Dean snorted. "Yeah. I remember. As soon as the snow was deep enough, we all went sledgin' up on the hill."

This appeared to be a safe topic of conversation. Nothing awkward or embarrassing here. Cas hummed his agreement."Right. And Gabriel always used to try and push me off my sledge."

"Gabriel's an assbutt," Dean said, scowling until the man beside him started chuckling, causing his expression to become surprised. "What? What's up?"

"Nothing." Cas sipped his coffee. "It's just...well, assbutt. I didn't think you would remember that."

Dean blinked at him. "Well...yeah. Of course I would. It was one of the best moments of my life."

"I told you that I loved you on that day," Cas mused absentmindedly, and then coughed as the air got caught in his windpipe when he realised what he had actually said. Dean was looking a little shifty too, keeping his eyes trained on his plate and the bottle of ketchup sitting next to it.

"Oh, yeah." His voice sounded vague, but his posture was way to tense for it to be believable. "I, er, I remember that now. That was...that was, y'know, good."

"Yes, it, it was, wasn't it?" Cas shuffled in his chair, picking at his own uneaten plate to avoid looking at the expression on his ex boyfriend's face.

 _Great. Well done, Novak. You just made everything three times as more awkward. Nothing that happens from now will make this -_

"Cas? _Dean?_ "

 _Oh, wow. I stand corrected._

"Hello, Jimmy," Cas greeted, finally having something to look at other than his food, for which he had suddenly lost his appetite for."What are you doing here?"

"I could ask you the same." The other Novak twin glanced between him and Dean. "Is this...Are you guys...?"

"What?"

"Spit it out, Jimmy," Dean said through a mouthful of food.

"Is this a _date_?"

Rather ironically enough, the mouthful of food was suddenly spat out of Dean's mouth. "Wha - _No_!"

"Jimmy!" Cas hissed at the same time, his cheeks flushing even more than they already were. "Shut up!"

"I only asked a question." Jimmy's expression looked innocent enough, but Cas could tell when he was trying to bite back a smirk, and he definitely was now. "Is this a date or not?"

" _No._ " The word was forced out through gritted teeth. Dean looked even more uncomfortable than when Cas had brought up the day that he told him that he loved him for the first time.

"Alright, alright, sorry!" Jimmy held up his hands, but he didn't look particularly sorry at all. In fact, he looked as if he was enjoying himself immensely. "I was just wondering! It's just nice to see you guys together again, that's all." He reached across to another table and snagged one of the chairs, pulling it up to sit beside his brother. Cas pushed the plate of unconsumed food towards him, and Jimmy happily began to tuck in.

"So," he said through his first bite. "What're you doin' up here so early, if not for a date?"

"Christmas shopping," Cas replied, and Dean nodded along in agreement.

"Awesome! So am I! Hey, maybe I can help you out?" He winked at the pair of them. "I am, after all, one of the best at matching the right gift to the right person."

Cas felt his shoulders sag, as Jimmy tore into the bacon roll once again.

This was going to be a long day.

* * *

 **Jimmy.**

 _They are so cute._

Jimmy smiled to himself as he watched Cas awkwardly hold up a trinket for Dean to comment on, before he placed it back on the shelf of the odd little gift shop that they had stumbled across. Not a date, his ass. If that was not a date, then he was the president of the United States. Which just went to show that his plan was working. Working better than he thought it would.

Not working fast enough, though, he thought, pretending to be looking at something when Dean's gaze went to him, returning to spying on them a few seconds later. They still hadn't admitted anything; hell, they couldn't even realise when they were out on a date, for Christ sake!

Clearly, the Destiel pie needed a bit of extra baking. Thank goodness he was a top quality chef these days.


	9. December 9th: Jimmy, Dean, Gabriel

_**December 9th: Jimmy, Dean, Gabriel**_

 **Jimmy.**

"I have an excellent idea," Gabriel announced suddenly to the collection of people in the living room.

Sam moved his head so that his chin was no longer nestled in Gabriel's blonde hair in order to look at him. "Oh, yeah? What's that, then?"

"We -" Gabriel gestured around the room "- should play hide and seek." He was met with silence. "Like, right now."

"Yeah. Right." Dean, who had, for once, bothered to join them on the couch in favour of sulking in his room, pulled a face. "Last time I checked, we weren't freakin' twelve again."

"Last time I checked, most of the people in this room could handle having a bit of _fun_ ," Gabriel quipped, eyebrow raised.

"I have plenty of fun."

"Dean, sexual escapades are not fun," Jimmy cut in, watching as his twin brother shuffled uncomfortably. Dean obviously noticed it too, because his cheeks suddenly looked a whole lot redder than they had been a few minutes previously.

"I wasn't talkin' 'bout _that_ kind of fun, Jimmy."

"You don't have any other kind of fun."

"I do!"

"Dean, sitting in the bar with Jo and drinking beer does not equate to fun. This is fun."

"A kids game is not fun."

"Well -" Gabriel interrupted, looking rather pleased with himself all of a sudden "- maybe we can make it a little more suitable. After all, Mama and Papa Winchester have gone out tonight. We've got the place to ourselves."

"That doesn't make it sound anymore appealin' that it was already."

"Lighten up, would you?" Jimmy rolled his eyes.

"He can't." Gabriel rose from his seat, taking two strides across the room and flicking the light switch, sending the room into darkness. "That would spoil the whole point, wouldn't it?"

Sam burst out laughing. "Is that it? We're playing in the dark? That's all you're doing to make this more "suitable"?"

"You'll start enjoying it once we get going," Gabriel replied offhandedly, returning to the couch and almost tripping over Sam's legs that were draped across the carpet as he addressed the others. "Me and Sam are gonna count to a hundred. You guys pair up and go hide. Hide somewhere good, though, not just behind the curtain or wherever. What would be fun about that?"

Jimmy looked at Cas' reaction again. The idea of hiding in a cramped space somewhere with Dean had made him look incredibly uncomfortable, and Jimmy wasn't sure whether he should be feeling happy about that or not. He was doing this for the greater good, though, he reminded himself. He wanted his little brother to be happy, after all, didn't he?

"Great." Dean, on the other hand, still sounded unconvinced. "Crouched in a corner waitin' for you and Sammy to stop makin' out before you eventually get 'round to findin' us. Yeah. Sounds like real fun."

"I don't think we're the ones that are gonna be making out," Gabriel quipped, holding his gaze on Cas for a second too long to pass as casual, before nodding towards Jimmy and Amelia. "I mean, come on, those two crazy kids will be going at it like nobody's business." He chuckled at his own joke, ignoring the dirty looks he got in response. "Now, c'mon. This isn't going to work if you don't join in." He clasped his hands over his eyes, motioning for Sam to do the same. "Right. Three, two, one...go." He cleared his throat. "One. Two. Three. Four. Have you moved yet? Five. Six..."

Dean exchanged a weary glance with Cas. "Guess we'd better go hide then." He walked out of the room without bothering to check if the younger Novak was even behind him or not. Cas followed him after a few seconds, rolling his eyes heavenwards and sighing as if the whole thing bothered him immensely - which it probably did, because everything seemed to bother Jimmy's twin brother.

Jimmy waited until the two others were out of the room, before he gave his older brother a shove, sending him into the couch and sprawled across Sam's lap, cutting off his counting.

"Hey!"

"What the hell was all that for?" Jimmy glared at his older brother.

"What the hell was all _what_ for?"

"All the _"Those crazy kids will be going at it"_ stuff! That wasn't part of the freaking plan!"

"I had to make it believable!" Gabriel pulled himself into a sitting position. "I couldn't make it look like I was picking on them, could I? That would have ruined the whole thing; you know full well what Dean's like, the awkward brooding ass."

"What do we do now?" Sam asked, shifting into a more comfortable position in order to support the sudden and rather unexpected weight of his fiancée. "How long do we wait until we go and fetch them?"

"Er..." Jimmy shrugged. "Not sure, really. I didn't think about that bit." He perched on the arm of the couch. "I didn't think this far ahead."

"What the hell happened to the _"You can't just throw the Destiel pie into a bowl"_ crap that you were spewing a couple of days ago?"

"Gabe, don't you know anything about cooking? Sometimes you can't just follow the recipe! You have to experiment a little bit too!" All he received was blank looks in reply.

Jimmy shook his head. His analogy talents were wasted in the Winchester household.

* * *

 **Dean.**

"I knew it."

Cas raised his head to look at him. "Knew what?"

"Sam and Gabe. They're too busy makin' out." Dean leaned his head back against the cold tiles of the bathroom, staring at the dark ceiling above them as they crouched in the shower. Cas worried at the sleeves of his trenchcoat, the one that always seemed glued to his body and that he was hardly ever seen without.

"Should we go and look for them?"

"Nah. They'll turn up when they're ready. Besides, I don't really want to make myself found quicker so that I get to spend more time watchin' them play tongue wars."

"Dean." Cas shot him a look. "Gabriel is my brother. I'd rather not think about such things."

Dean snorted. "Bit late for that. They're gettin' married soon. We won't be able to escape it then. It'll be everywhere. Well, I won't be able to escape it. You'll be back in Pontiac by then." He tried to speak lightly, but a bitterness clouded his tone.

Cas sighed. "Dean..."

"I know, I know. Forgive and forget an' all that. Let bygones be bygones. Mom's been tellin' me the same thing for years." His phone buzzed in his pocket, cutting him off from saying anything else. He pulled it out to look at the screen, squinting at the sudden brightness in the otherwise dark room.

 _Hey, Dean. I know you said that you'd call and everything, but I was just wondering if you perhaps wanted to come over on Sunday? I'm doing dinner again, and I think it would be nice to get to know you better. Let me know what you think. Lisa. X_

"Is it Sam and Gabe telling us not to disturb them?" Cas asked after a few moments of silence.

Dean raised an eyebrow, momentarily distracted. "Damn. Didn't think you'd be one for a dirty mind, Cas."

"What can I say?" There was something of a mirthful smile on his face. "College broadened my horizons."

"Oh, yeah? For the better?"

"Not sure. In the long run, yes, I suppose it was. Although, being hung over for the first time wasn't particularly pleasant, to say the least." He shook his head as Dean nodded.

"Ah. I feel you there, buddy." He glanced down at the grey message bubble on the screen, only looking up again when he felt Cas watching him with an unidentifiable expression. "What?"

"You called me buddy."

"Well...yeah."

 _Great. Real smooth, Winchester._

"You haven't called me that in years."

"Yeah, well...Old habits die hard, I guess." Dean cleared his throat and looked down at his phone yet again. His face must have shown his emotions, because Cas suddenly spoke up.

"Something the matter?"

"Hm?" Dean hummed absentmindedly. "Oh. Nah. Just talkin' to Lisa."

"Lisa?" His head snapped up once he registered Cas' tone: wary, cautious, almost wounded. "As in Lisa Braeden?"

"Yeah. How'd you know?"

"Your friend Jo might have mentioned it." Cas' fingers pulled at his sleeve, a quirk he'd had for years. Tugging on his sleeves meant that something was bothering him. "She wanted to set you up with her." It wasn't a question.

"Yeah. Jo has a tendency to do shit like that. It's never gone particularly well." None of the friends that Jo had tried to fix him up with in the past had ever contacted him after that first meeting.

"Are you going to see her again?" Cas asked - or rather, demanded.

"I don't know. ? What's it to you?" He sounded harsher than he had meant to. _Way to rub it in. Good going, Winchester._

"Nothing." Cas rested his weight against the wall, his voice muttered and a little sulky until he spoke again. "Nothing at all."

"Cas -"

"I, um, I ran into someone today too, actually."

Cas was a terrible liar. Dean could tell almost immediately when he wasn't being truthful, even in almost total darkness. "Oh?"

"Yeah. Do you, uh, do you remember Meg Masters, by any chance?"

Dean snorted. Meg Masters had been a classmate of theirs, once upon a time, and hadn't spoken a word to Cas since they broke up when they were fifteen; she didn't exactly strike him as the chatty reunion type of woman now, on the odd occasion that he saw her out and about.

"Meg's not exactly easy to forget. What about her?"

"Oh, y'know." Cas shrugged, trying and failing to sound nonchalant. "I was thinking about grabbing coffee with her one day. What do you think?"

 _I think it's kind of sweet that you're trying to make me jealous_ , was the first thing that Dean thought. He didn't say it out loud, though. It was awkward enough just knowing about Cas' hopeless crush without indulging it.

"Doesn't matter what I think, Cas. S'your life. You do whatever you want."

"Hm." Was all he got in response, until, "I've had enough. I'm going to go and see what's taking so long." He rose from his position, stepping out of the shower and disappearing through the bathroom door, not even bothering to turn the light on as he did so.

* * *

 **Gabriel.**

"Jimmy?"

The younger Novak looked up from the mug of tea he was making. "Yeah?"

Gabriel was leaning around the kitchen door frame, looking tenser than usual. "I don't want to doubt your expert chef skills, but I think you missed out a couple of stages in the Destiel pie."


	10. December 10th: Gabriel, Crowley

_**December 10th: Gabriel, Crowley**_

 **Gabriel.**

"Who the _fuck_ does he think he is?" Jimmy said for what was possibly the thousandth time, slamming the door to the Roadhouse as he marched through them. "Does he think that this is funny? Does he actually have no idea what the fuck is going on?"

"Whoa, Jim-bob." Gabriel followed a few paces behind him, eyebrow raised. "Calm down. I'm not entirely sure that the situation calls for all this -"

"Oh, yes. It does." Jimmy perched on a bar stool, scowling as he gestured to Ash for a shot of whiskey.

"Girl troubles?" Ash asked sympathetically, sliding the glass across the counter.

"I wish," the younger Novak grumbled. "More like brother troubles." He reached for the shot and downed it in one, nodding for another one as Gabriel sat next to him.

"So, what does this mean? Is the plan off?"

Jimmy almost choked on his second shot, staring at his brother incredulously. "Off? Is the - _Off?_ No, it's not _off!_ It's never going to be _off!_ Dean and my brother are admitting that they still love each other whether they like it or not!"

"Okay, okay, chill out!" Sheesh. Jimmy had an ever larger stick in his ass than Castiel did. "Just saying. Doesn't exactly make things easy now that Lisa Braeden's involved."

"Yeah, well, she better get uninvolved." Jimmy was on his forth shot by now, throwing the glass aside and reaching for the fifth that Ash wordlessly passed to him. "I refuse to let my brother become heartbroken let again - I _REFUSE_ -" He cut himself off by slamming his palm down onto the bar counter.

"I feel ya, buddy." Ash shook his head. "I've been tryin' to get Jo interested in this friend of mine for years, and she just hasn't taken the hint." He pushed a bottle of beer towards Gabriel, who gratefully opened it and took a long gulp. He was going to need it once Jimmy had finished.

"What do we do now?"

"Well, I don't know about you, Gabe, but I'm drinking until I get another good idea."

"Yeah, I don't think that's such a wise move, Jimmy. I don't particularly want to have to haul you away from another farmyard."

"I think you guys are just making that bit up, to be honest. I have no memory of it."

"You were too intoxicated to remember it. But that's not the point. The point is that we still have no idea what we're going to do about Dean and Cas."

"Actually, gentlemen -" A voice cut across their conversation before the younger Novak could respond; both glanced to see a man in a dark suit leaning against the bar a few metres down from them "I think I might be able to offer you some assistance there."

Jimmy looked miffed at being interrupted. "Who the hell are you?"

The man chuckled, holding out a hand. "Allow me to introduce myself. Crowley. Business executive."

"Uh hu," Jimmy replied, unconvinced.

"Crowley..." Gabriel frowned. "Aren't you that douchebag part-time mechanic that my brother-in-law has been constantly complaining about for the past three months?"

Crowley paused for a moment, before dropping his outstretched hand that neither brother was going to accept. "Business executive, part-time mechanic...What's the difference, really?"

"I can think of a few differences."

"Going by the snarky attitude, I guess you must be James."

"It's Jimmy."

"James, Jimmy, it all means the same thing. But, that's not important right now. What is important is how much use that I could be to you in your little matchmaking endeavours." A smirk crossed his face. "For a price, of course." The two brothers exchanged a look before glancing back to Crowley.

"Alright," Gabriel said after a moment. "We're listening."

* * *

 **Crowley.**

"This is ridiculous," Jimmy grumbled.

"You were the ones who agreed to the deal," Crowley replied simply, grinning at the sight of the two Novaks in greasy overalls, the ones that he refused to wear. "I'd talk to Squirrel if you agreed to fix up the cars for a day."

"You know that Jim-Bob and I know next to nothing about fixing up cars, right?"

"I don't care how well the job is done. Just as long as it gets done. Plus, I can guarantee that you two chuckleheads will know more than I do."

"Why did you even apply for a job here, then?"

"I didn't. Bobby offered me employment here."

"Yeah, right." Gabriel let out a snort. "Bobby would never willingly employ someone who was as crap at mechanics as you."

"Okay. Maybe it wasn't quite as honest as that. Bobby owed me a favour from our college days and three months ago, I came to collect."

"What sort of favour?"

"To make a long story short, our college days were a little wild, and I came into possession of a very incriminating photograph. In order to keep it hidden, Bobby offered me a part-time placement here at the garage."

"That's fighting dirty, Crowley."

"Yeah. Hardly professional."

"Who said anything about me being a professional?" Crowley replied, snorting as he headed in the direction of the office, where Dean was busy sorting through some paperwork that Bobby had left for him.

"Squirrel," he greeted.

"King of Hell," Dean replied. "Aren't you supposed to be fixin' up the cars out back?"

"Trust me, I've got my best team on it."

"Hm."

Crowley leant against the desk, watching him organise for a few moments before speaking again. "I was like you once, Squirrel."

"I doubt that, but go on."

"I was young. I was popular. I was a hit with the ladies - Don't pull that face! I saw the fun in relationships, to have that one person ruin your life forever more. And there was one in particular. My best friend. We met in college and grew very fond of each other, I myself too fond, perhaps."

"My heart bleeds for you," Dean snorted, but there didn't seem to be as much bite behind the words as there might have been if Castiel Novak had remained in his Pontiac exile.

"Your mocking does nothing except fuel my story, Squirrel. Anyway, as I was saying, it wasn't long until I realised my mistake. Growing too fond of anyone is incredibly dangerous, I've learnt. Can lead to all sorts of nasty things. All sorts of feelings."

"Sometimes feelin's are more trouble than they're worth," Dean cut in.

"Exactly! Certainly true in my case." He shifted so that he was closer to the Winchester. "Contrary to what you might see now, Winchester, I wasn't exactly the most outspoken child in my college class. Which is why I never told my dear friend about my festering affections. I had to watch her fall in love with the star quarterback from high school and marry him in a registry office. Now they've got three kids together."

"So?"

" _So_ , Squirrel, I wish I'd had the courage to tell her how I'd felt before it was too late. Maybe she wouldn't have returned the affections, but I wouldn't have sat there in pain whilst I watched her promise to love and honour someone else. Dean." The sound of his real name made Dean look up, his hands pausing entirely. "Don't make the same mistake I did." He nodded once to affirm his words, before pushing off the desk and strolling out of the office, smirking as he felt Dean's eyes boring into his back.

 _Some people will believe anything._


	11. December 11th: Castiel, Dean

_**December 11th: Castiel, Dean**_

 **Castiel.**

Clearly, spending seven years in Pontiac had given him a death wish.

Cas stuffed his hands into his trenchcoat pocket as he nudged the door to the convenience store open with his hip, eyes set on the counter on the far side of the room, where Meg Masters was slouching, eyes staring down at the phone in her right hand. He hadn't seen her since they had left high school, and seven years had certainly changed her, her blonde hair now down past her shoulders in a dark brunette colour, her frame thinner, her nails now long and painted.

He reached for something blindly off the nearby shelf, clearing his throat as he went up to purchase it.

"I'd like to buy this, please."

"Wait one second." Meg's thumb flew across the screen as she typed out a message.

" _Meg._ "

This made her glance up. She did an double take, before a smirk settled on her face. "Well, well, well. _Castiel Novak_. Scrubbed up well, haven't you?"

"You too. It's been a long time."

"Hasn't it just?" She tapped her long fingernails on the counter, eyebrow raised at the product still in his hand. "It really, really has, apparently."

"Hm?" Cas glanced down at the box of diapers he was currently clutching. "Oh - No, no, no, these aren't-"

"Calm down, Castiel. There's nothing to hide in this town. It'll get out one way or another. I'm sure Dean makes a great father to the little one."

 _Oh sweet Jesus Christ._

"No, no, these aren't for us - I mean, for _me_! They're not for me." Cas tried not to cringe at the fact that he'd just referred to Dean and himself together, as if they were still a thing. "They're for...a friend of mine."

"Uh hu." Meg grinned, clearly having too much fun with her jib to give it up. "Bit dreadful at diapers, is he? Don't worry yourself about that, Momma Cas, Dean will settle into it soon enough. The men always do. Give it some time."

"Me and Dean broke up years ago, Meg. Just before I left."

"Really? Now that is a surprise." She didn't sound very surprised at all. She must have heard it from somewhere; nearly everyone in their immediate circle knew about the mess that Cas and Dean's relationship had become. "I thought you guys were gonna be the ones, y'know? That one couple who outlived high school and got married, did all that kid crap. Guess I was wrong, huh?"

"Guess so."

"Should have just stuck with me, Clarence. I wouldn't have dropped your sorry ass when you tried to leave. I'd have waited for you instead of sleeping with everyone I could lay my hands on."

Okay. If Cas hadn't realised how much of a mistake this was on the way in, he certainly understood now.

"He didn't _drop my sorry ass_ ," Castiel replied vehemently. "We mutually went our separate ways."

"Don't give me that bullshit. Jo Harvelle told me what happened. You two had some massive fight and then you cried your way to Illinois and left Dean here to drink himself to death."

"I didn't!"

"I think you'll find that you did. Nothing gets past me, Clarence." Meg gave a conversational shrug. "But no matter. All over and done with, yeah? In the past. Forgotten about." She beamed at Cas' expression, as if the whole conversation suddenly hadn't happened. "So, you buyin' those diapers or what? Business is booming, and you're stopping me from serving the other customers."

If he hadn't been in the mood he was suddenly in, Cas probably would have taken the time to point out that there were no other customers in the store. "Sure," he said instead, voice clipped and snippy, dumping them on the counter, just desperate to get out of the store without any fuss. "How much?"

"Usually two dollars -" Meg winked at him "- but, because you're special to me, you can have a dollar off."

"How generous."

"I really am, aren't I?" Meg scanned the diapers and took the dollar bill that Cas handed to her. "Well, this was a pleasant experience, wasn't it, Clarence?"

"Yeah. Pleasant." Cas took his purchase without another word, and turned on his heel.

"Bye bye now!" Meg called after him as he slammed the store door.

* * *

 **Dean.**

Dean wasn't exactly surprised when he saw Castiel's car parked on the sidewalk outside of the convenience store where Meg Masters worked. After their conversation a couple of days ago, and Crowley's tale of heartbreak yesterday, his relationship with Cas had been playing on his mind - well, more so than usual. He'd realised, shamefully too late, what exactly Cas had been so upset about during the game of hide and seek, and smacked himself on the back of the head when he'd worked it out. How could he have overlooked Cas' crush on him? If he was in that same position, he would be upset too.

Which, he wasn't, of course.

Because he didn't have a crush on Cas.

And that totally wasn't why he'd hopped out of the Impala and was now hiding behind one of the shelves in order to overhear his conversation with his high school girlfriend.

Not at all.

"No, no!" Cas was saying. "These aren't for us - I mean, for me! They're not for me." Dean checked to see what "they" actually meant. What was Cas doing buying diapers, of all things? "They're for...a friend of mine."

"Uh hu." Meg Masters sounded amused, far too amused at Cas' discomfort for her own good. "Bit dreadful at diapers, is he? Don't worry yourself about that, Momma Cas, Dean will settle into it soon enough. The men always do. Give it some time."

 _Momma Cas? Does she think that...?_

"Me and Dean broke up years ago, Meg," Cas informed her, and Dean swore that he wasn't imagining the note of sadness that those words held. "Just before I left."

"Really? Now that is a surprise. I thought you guys were gonna be the ones, y'know? That one couple who outlived high school and got married, did all that kid crap."

 _So did I_ , Dean thought.

"Guess I was wrong, huh?"

"Guess so," Cas agreed, not sounding too enthusiastic about it.

"Should have just stuck with me, Clarence. I wouldn't have dropped your sorry ass when you tried to leave. I'd have waited for you instead of sleeping with everyone I could lay my hands on."

Dean gritted his teeth as he listened, fists clenching around the newspaper he was pretending to study. Now he remembered why Castiel had broken up with Meg in the first place. But, then again, he'd always considered her an utter bitch. Of course, she would try to side with Cas in something like this, wouldn't she? Even though Cas had left him without so much as a goodbye, not even a phone call. The radio silence had hurt Dean more than any words that Cas had spoken to him.

"He didn't _drop my sorry ass_. We mutually went our separate ways."

"Don't give me that bullshit. Jo Harvelle told me what happened. You two had some massive fight and then you cried your way to Illinois and left Dean here to drink himself to death."

 _Leave him alone, bitch._

"I didn't!" Cas insisted, but he couldn't disguise the guilt in his voice. It made the same emotion begin to seep into Dean's own stomach.

"I think you'll find that you did. Nothing gets past me, Clarence. But no matter. All over and done with, yeah? In the past. Forgotten about." She paused for a moment. "So, you buyin' those diapers or what? Business is booming, and you're stopping me from serving the other customers."

Dean realised that she was talking about him. I wouldn't buy anything from your store even if you told me that everything was free, bitch, he thought bitterly, watching as Cas passed over the money for the unnecessary diapers and stalked out of the store. Dean waited for a moment, before he charged after him, slamming the door behind him for good measure, just as Cas had done a few seconds earlier.

"Cas!" He called out, startling the man who was angrily trying to cram diapers into his car.

"Dean?"

"Are you okay? I heard what Meg -"

"Fine." Cas cut him off with a hard stare, his brow creased. "Nothing to worry about. Just Meg being Meg. I was stupid to try and converse with her." He glanced over his shoulder slightly before continuing. "Don't worry about me, Dean. I'm honestly fine. I'll see you back at home."

"Cas -" Dean stopped him yet again, grabbing him by the arm. "Why did you try and talk to her?"

"Well, why shouldn't I?" Cas tugged his arm away, narrowing his blue eyes into slits. "Am I suddenly not _allowed_ to talk to others, Dean? Is it one rule for you and one for me? Is that how breakups work with you?"

With that, he stormed around to the drivers side and got in, slamming the door and pulling off the sidewalk sharply and leaving Dean watching after him.

"Cas!" He called after him, despite the fact that doing so was pointless, before he kicked the sidewalk with the cap of his boot. " _Shit._ "


	12. December 12th: Jimmy

**Just Jimmy today! I loved writing Jimmy** **'s perspective for this day and getting to be both jokey and serious; he might be my favourite character in the whole of SPN if I had to pick just one. #JimmyAndHisSass X**

* * *

 _ **December 12: Jimmy**_

 **Jimmy.**

Jimmy rapped his knuckle on the open bedroom door that belonged to Dean."Hey, Cas."

Cas smiled."Hello, Jimmy. What can I do for you?"

The other Novak twin shrugged. "Amelia and I are about to head off, go get some decorations for Mary and maybe a few other bits and bobs for Christmas presents. You want to come with us? I remember you saying that you didn't find anything last time that you went. There's plenty of places we haven't checked out yet, and Amelia spotted this store where you could get some engagement stuff for Gabe and Sam -"

"Oh, no. Thank you, Jimmy, but it's alright."

"Are you _sure_?" Jimmy leant against the door frame, arms folded, watching his twin brother who was sitting on the floor with his legs crossed, tapping away on his laptop, eyes fixated on the screen in front of him. "Because you're welcome to come - you know that, right? That you're always welcome?"

"I'm quite sure, Jimmy," Cas replied. His voice sounded bright and even, but Jimmy was a twin. He could tell when Castiel wasn't feeling right, even when he didn't announce it to everyone, and this was definitely one of those times. "Besides, I wouldn't want to bother you or get in your way."

"You wouldn't bother us." Jimmy frowned at that. "Or get in the way. I mean, Christ, you're my brother; if I couldn't put up with you, I would have told you a long time ago when we were, like, ten, not waited until we were in our mid-twenties and watching middle age edge ever closer on the horizon."

Cas' lips twitched into what could have been a smile. "All the same, I think I would like to stay here. I've got a lot on my mind, and it won't stop irritating me until I sort it out."

"Yeah, okay, but, are you _really_ sure?" Jimmy insisted.

"Of course! Why wouldn't I be?"

"Well, you haven't even left this room since yesterday, Cas. All you've been doing is just working on that damn computer of yours for hours on end. That's not exactly healthy."

"Neither is ice cream, nor is chocolate. People still have those at Christmas. This is just my version of cookie dough, if you think about it."

"Okay, now you're just being a little shit for the sake of it, aren't you? Look, Castiel, if this is about Dean and his stupid dinner thing tomorrow night, then you should really just ignore it -"

"Jimmy." Cas did glance up from the screen then; Jimmy couldn't help but notice the dark circles that ringed his eyes, left over from a lack of sleep. "I'm _fine_. Honestly." _Lie._ "This has nothing to do with Dean." _Lie_. "I'm just behind on some documents that I promised Hester I'd do before Christmas Eve. Once I'm done with these, I'm all yours again. Promise."

Jimmy didn't believe him for a second. Not for one goddamn second. His twin intuition told him all that he needed to know. But he nodded once, stuffing his hands into his pockets. "Okay. Sure, buddy. Whatever you want to do is fine. Do you need me to pick anything up for you?" Cas merely shook his head, already engrossed in the documents that Jimmy couldn't see. "Okay. Well, see you later, then."

"Hm." Was all he got in response, the sound chasing after him as he began the descent down the stairs.

Amelia and the others were waiting for him in the hallway. Her face was lined in concern as she observed his expression. "Is he...?"

"No." Jimmy heaved out a sigh. "He's insisting on staying in that damn room."

"Oh, Cassie..." Gabriel shook his head as he muttered to himself, glancing up towards the landing. "You freaking idjit." Sam rested a hand on his shoulder and squeezed comfortingly.

Jimmy ran a hand down the length of his face. "Jesus Christ, what have I done? What if it's my fault?"

Amelia's eyes widened. "Don't say that!"

"I'm serious! I was the one who was all " _DeanCas Pie_ " and " _The plan is never over_ " and all that bullshit. Now my twin brother is sitting in that stupid room with that stupid laptop, hurting, and won't come out, all because of me. What if I've just made a bad situation worse?"

"You couldn't have made it worse than it already was." Her voice was firm. "It's no where near as bad as it was when we first got here."

"How? They're not even speaking to each other anymore. Dean's been disappearing off to the bar and is gonna start getting it on with Lisa Braeden. We're as far from getting them back together as its possible to be; any progress we ever made was just set back three freaking thousand years."

"Not to mention I spent the entire day on Thursday fixing up cars for nothing," Gabriel commented. "Whilst you sat on the sidelines and watched."

"If that is true, then it isn't just your fault," Sam jumped in loyally, ignoring his fiancée's jibes about their escapades a few days prior. "We'd all be to blame in this situation - you, me, Gabe, Amelia, hell, even Dean and Castiel. They were the ones who had that stupid fight all those years ago in the first place and started this entire thing."

"Yeah, but -"

"But, nothing," Sam insisted. "Don't you dare try and take this on yourself. I think you'll agree that we've all had enough of assigning blame to people, whether it be ourselves or others, over these past seven years, yeah?"

Jimmy looked between the others, before letting out a sigh. He still felt responsible - how could he not? Cas was his twin brother, his mirror image; when one was hurting, the other hurt just as much, maybe even more - but one look at the expression on their faces told him that he better suck it up and deal with it, because he wasn't taking all of the blame.

"Fine," he said after a moment. "I suppose you're right."

"We are right," Amelia replied. "And you know that we're right. So, get that look off your face, James Novak, and let's go, because the day is slipping away as we speak and Christmas is not going to wait for us." She threaded her arm through his, calling goodbyes to Sam and Gabriel over her shoulder as she bustled Jimmy out of the front door and towards Cas' car, parked wonkily on the edge of the sidewalk.

She was right, of course. Christmas was less than two weeks away now. And Jimmy did try, really he did, to get into the festivities as they wandered around the small designated shopping area for the town of Lawrence, but his mind kept wandering back to Cas and Dean, to the whole messed up situation, to the dark circles under his brother's eyes that he'd tried to pass off as nothing.

"You're still feeling guilty about Cas, aren't you?" Amelia asked eventually, when they were settled into a window booth in the nearby diner, distracting Jimmy from his absentminded staring out of the glass at the cars and pedestrians travelling past them. He gave a nod, reaching for his coffee and taking a long gulp from the chipped ceramic cup.

"It's not just guilt, though."

"What is it?"

"I'm worried about him too. I mean, I'm always worried about him, of course I am, he's my brother, but, ever since we got here, he seems...I don't know. Different? D'you know what I mean? Like, Cas has always been...the sensible one, I suppose? The one who had everything down. He knew what college he wanted to go to from the age of ten. He sorted out housing for us. He never freaks out, in front of me, at least. He's always calm, practical. Stable, even, I guess you could say. I drifted through my teens with no idea of the real world, and Cas was always the one that kept me on the straight and narrow. And now..." He trailed off.

"Now he's all over the place, you don't know what to do," Amelia finished.

"Yeah. Something like that. I can't help it. It comes from being half of a set of twins. When one's not right, the other isn't right, y'know?" He tipped some sugar into his cup, using the paper to blend it with his drink. "I've never seen him more right than when he was with Dean. When they were dating, I mean. Now he's all over the place when he's around Dean - but, who can blame him? Back then, though, if anything, being with Dean kept him even more stable." A smile flickered across his face. "They were so good together. And so cute too. I remember this one time, it was senior skip day. Lawrence High School tried to round us all back up and cart back to classes for the day, but Gabe hijacked Bobby's van and the four of us went to the woods for the day. Took a picnic and everything. Thought we were so cool." He snorted. "We looked like a group of idiots, really, especially when me and Gabe were both wearing shorts to hike in, and Cas was in that stupid trenchcoat. But, it ended up being a great day. Gabe and I complained about it non-stop when we were there, but Cas and Dean were the most adorable thing you've ever seen. Straight outta one of those sappy romance flicks. Feeding each other food, wiping crumbs from each other's mouths, the entire thing. It was a wonder that they didn't start trying to get off whilst we were there too." Jimmy shook his head. "Sometimes I wish we could go back to those days. I've never seen my brother happy like that again since those two dumbasses broke up."

"Even if you had to wear the hiking shorts again?"

"I would wear ten pairs of rainbow hiking shorts at the same time just to see my brother happy like that again." Jimmy sipped his drink. "I thought they were gonna last forever, y'know? They fit perfectly. Like true love and all that. I think Cas thought that they would last forever too."

Amelia reached across the table to squeeze his hand sympathetically. "Maybe they still can."

"Yeah, right. Not after the complete fuck-up I made of trying to get them back together."

"That doesn't sound like you at all. Last time I checked, James Novak didn't give up so easily, _especially_ when it came to cooking."

"I think my cooking days are over."

"Maybe you just need to take a new direction." There was a gleam in her eyes as she spoke. "Maybe you need to start showing Cas how to cook first."

Jimmy frowned at her for a moment, before he cottoned on the cooking metaphor and a grin spread across his face. "Jesus Christ, you're right."

"You're welcome."

Jimmy rolled his eyes, leaning across the table to kiss her briefly. "Do you know what we need to do, my dear?"

"What?"

"We need to get Cas out of his room. Get him to the Roadhouse whilst Dean's having his dinner with Lisa, and get his mind off of it."

"What about getting Dean and Cas back together? Have we given up on that plan?"

"Nope. I told Gabe that the plan would never be off, and I've just realised that we need to stick by that. We just have to come at it from another angle, that's all." He raised her knuckles to his lips and kissed them too. "Were you always this smart, or have I just gotten stupider?"

"What can I say, Jimmy?" Amelia beamed at him from across the table. "You'd be lost without me."

* * *

 **I love Jimmy and Amelia (Jimelia?) so freaking much. Novak power.**

 **Until tomorrow, my little sock puppets :) XX**


	13. December 13: Lisa, Castiel, Dean

_**December 13: Lisa, Castiel, Dean**_

 **Lisa.**

"Okay, Dean, enough." Lisa slammed her glass down on the kitchen counter, startling Dean out of his thoughts, yet again. "What's been going on? Why did you agree to come here today?"

"Huh?" Dean's brow furrowed. "I don't know what you're talkin' 'bout. I'm here 'cause I wanted to be."

Lisa let out a sigh. Seriously. Why were the cute ones always so slow? No, forget that, why were the cute ones that _Jo Harvelle_ set her up with always so slow? Sometimes, Lisa felt like her best friend simply wanted to torture her by doing stuff like this. Dean Winchester appeared to be no different. Which was a pity, really, because Dean was _really_ cute, but, hey, what could you do?

She rolled her eyes. "Don't try that crap with me. You know exactly what I'm talking about. You've been zoning out on me since the moment that you got here, so what's up? You got somewhere else to be?"

"Nothin''s up."

" _Nothing_ , huh? Sure seems like nothing; maybe that's why you've been gazing out of the window at every opportunity you've got? What's the matter?" Her voice took on a brief jokey tone. "Are we that boring company?"

"No, no! 'Course not!" Dean corrected hastily, drying another glass and placing it back on the top shelf of the nearby cupboard. "Just got a lot goin' on right now, y'know?"

"Uh hu." Lisa folded her arms. "Like what?"

"Oh, y'know..."

"No, Dean, I don't know. That's why I'm asking."

"It's just stuff. Like, personal stuff. My own personal...I don't know what to call it. Crap."

"Right. And does this " _stuff_ " involve Castiel Novak in some way, shape or form?"

Dean's immediate groan in response was as good as a verbal yes. Lisa shook her head, pushing her dark hair from her eyes. She could remember Castiel vaguely from high school, a shy, rather socially awkward student who ran the chess club and partially lived in the library and whom Dean had utterly adored with what seemed to be every fibre in his being. Well, at least he had, until Cas had left all those years ago. It was for this very same reason that Lisa had originally had qualms about Jo trying to set her up with the now single Winchester. Clearly, she was right to. No matter what he said, Dean obviously still had some kind of feelings for Castiel; anyone with a flicker of common sense could be able to tell that.

"Lisa. Please. I don't want to talk about this."

"So you'd rather wallow over it in silence, then? Great plan, Dean."

Dean sent her a look. "I've wallowed in it for a long time. Why stop now?"

"Your own mental health, maybe? C'mon, Dean, spit it out. It can't be that bad."

The Winchester paused for a moment, hands stilling over the piece of cutlery that he had been drying, before he exhaled heavily. "Okay, okay. It's kind of a long story, though."

"I can listen." Lisa raised an eyebrow, propping her elbows up on the counter and leaning forward, almost eagerly.

"I overheard Sammy and Gabe talkin' outside the bathroom about a week ago. I didn't think anythin' of it at first, but then I realised what they were sayin'. They said that Cas had a crush on me and was freakin' out because he didn't know what the hell to do about it."

Lisa's brow creased slightly. "That would make sense. Y'know, considering how he left the Roadhouse that night last week."

"What night?"

"You know, the night we met? That party that the Harvelles put on? Jo kind of pushed us together and then wandered off to talk to him - I think you were talking to Ash at this point and ordering drinks? - but I saw him looking over at us and then leaving in kind of a hurry. I thought at the time it was because he needed to puke outside or something. Hell, I didn't even recognise him until Jo found his brother on Facebook and showed me a picture."

"Really? That happened?"

"Do you think I'd lie about something like that?" Lisa questioned, before poking him in the arm before he could let out a groan and slide back into his inner monologue. "Don't stop there. What happened next?"

"Well, the next day I saw him on the way home. I didn't know why I did it, but I pulled over an' offered him a ride, which was freaking awkward as hell. We went Christmas shoppin' the next day too; that was pretty uncomfortable too, especially when that idjit Jimmy turned up too and started makin' all these comments. Cas didn't particularly like the fact that his little secret was bein' announced to everyone. He went as red as the freakin' ketchup bottles on the table. It was kinda cute, actually -" He stopped suddenly at the smirk on Lisa's face. "I mean, um - I felt kinda bad for him, y'know? Jimmy did the same thing to me back when we were in high school. He'd make all these comments about me " _bein' sweet on his brother_ ", as he kept puttin' it."

"That's adorable."

"More like humiliatin'."

"You're just too close to see it," Lisa replied, waving her hand in a dismissive fashion. "So, go on. What happened next?"

"Well, Gabe suggested that we play a game of hide and seek - Yeah, I know. Don't gimme that look. I got roped into the whole thing. Anyway, me and Cas hid upstairs and we ended up talkin' 'bout you an' dinner - Ow!" Lisa had reached out and whacked him on the arm as soon as the words had left his mouth. He rubbed the patch of skin to alleviate the stinging. "Jesus Christ, Lisa, give a guy some warnin'. What the hell was that for?"

"You mentioned dinner tonight in front of the guy _who has a crush on you_ , Dean?"

Wow. Dean Winchester was more than just slow. He was oblivious.

"Yeah, now you put it like that...does seem a little bit of a dick move."

"A little bit?"

"Okay. A lot of a dick move. But, I didn't realise that at the time, and only had that mental breakthrough later. Anyway, a couple o'days ago, I went to the store to pick up some stuff and saw him there, talkin' to that Meg Masters chick."

"And?"

"Well, I never liked her - she was a bitch, so that wasn't my fault - and she sure as hell didn't like me. She started sayin' all this stuff, and Cas kind of freaked out. And now he won't leave the house, or even the damn room - he just sits in the corner and works constantly -"

"And you let him?"

"Well, yeah, but - Ow!" He winced, massaging his arm once again. "Sheesh, Lisa, it wasn't like that! He's not even speakin' to me!"

"Yes. And who's fault is _that_?"

"Okay, okay, point taken! But, still, I don't know what to do 'bout it. I mean, c'mon, the guy won't speak to me. How am I supposed to make amends?"

Lisa thought for a moment, tapping her chin with her index fingers as she hummed. If it were anyone else, she would have said something more stereotypical - chocolates, flowers, a boom box playing outside of a window, that sort of thing - but this was Cas. Cas Novak, who had spent almost three years obliviously blundering through life whilst being unaware that Dean Winchester was revering him on the sidelines and hopelessly pining after him. Normal, stereotypical methods wouldn't work.

"I'll tell you what you gotta do," she said finally. "Get your ass back to your house right this instant, sit in the damn room that Cas won't leave, get on your knees and freaking grovel for him to forgive you."

"Now, hang on -"

"Dean, this is not a time for your masculine pride to get in the way. Trust me, if Cas won't speak to you, you have to speak to him. Get in that room and just talk. He may not respond straight away, but he'll hear it, and he'll know. He's never not listened to you. And before you say anything, close the door if you don't want anyone to see you begging for forgiveness." Dean promptly shut his mouth. Lisa rolled her eyes. "Go on. Get your ass outta here. I'll finish up."

"Are you sure? I should at least stay and help you clean up -"

"No. Because I know you'll chicken out given enough time." She folded her arms. "One condition, you gotta call and tell me how it goes, yeah?"

Dean released the breath he'd been holding in, and flashed her a smile. "Yeah. Whatever you want. Thanks, Lisa."

"Just call me Matchmaker Extraordinaire," she said with a grin, before pulling a face seconds later. "On second thoughts, don't call me that. Ever."

* * *

 **Castiel.**

"Cas!" A banging came from the bedroom door. Cas jumped slightly, his head flying off the keys of his laptop (not that he'd been sleeping or anything.)

"Jimmy? What are you - Is something wrong?"

"Yes. Something is wrong. With you." His twin brother stalked into the room without any warning, plucking the laptop from Cas' fingers and dumping it onto Dean's bed, slamming the lid down with a clatter.

"Jimmy -!"

"Cas, you are my brother. My twin. My mirror self. I love you, buddy, which is why I'm not going to just sit downstairs and let you wallow in self pity up here all alone."

"I'm not -!"

"Cas, when was the last time that you had a shower? Put on clean clothes? Had something to eat? Look at you! You're the most wallowing wallower that ever wallowed in the history of wallowing."

"I'm not sure that's a real term, Jimmy."

"I don't care! You're not sitting in this room alone for a minute longer." Jimmy nodded firmly to reaffirm his words. "And the first thing that we're going to do is get you into the shower - don't even try to argue with me on this - and then we're all going out. The Roadhouse do some really nice meals around this time."

"Jimmy -"

"What did I just say about arguing with me on this? C'mon, if you won't listen to me, I'll get Gabriel in here."

"I don't want to go if Dean's there." The words even sounded lame to Cas' ears, but he couldn't help it. It was the truth, after all.

He expected Jimmy to roll his eyes, but instead, his twin brother squeezed his shoulder. "Well, don't worry. He's not coming with us. It'll just be you, me, Amelia, Sam and Gabe. That sound better?"

The tension began to drain from Cas' shoulder. "Hm. That does sound nice. Alright."

The two brothers shared a smile. "Cool. Don't worry about a thing, Cas. I'll take care of it all."

* * *

 **Dean.**

"Hey, Jo." Dean slouched on the bar stool with a sigh.

"Winchester! Back so soon?" Jo winked at him as she slid a beer towards him. "I thought you were done with all your moping? Whoa." She nodded to the flowers that he'd laid out on the desk - pink roses, tied with a decorative bee ribbon. "Nice. Who you tryin' to impress?"

"No one, apparently," Dean grumbled, taking a long swig of the drink in front of him. He'd spent a long time thinking about Lisa's words during the drive home, and he'd eventually come to the conclusion that, if he was going to do this and grovel for Cas' forgiveness, he was going to do this right. Which was what had led him to taking a detour on his travel back to the house, during which he had spent many minutes trying to pick out a bunch of roses that would accurately represent what he wanted to say. Not red, because he wasn't going for the sexual approach, and not white, because it wasn't their freaking wedding day (and also because Dean certainly had not fantasised about that a few times over the years - he _had not_ ). In the end, he had gone with pink. That accurately represented his current feelings towards Cas, right?

He realised, as soon as he got inside, that he shouldn't have wasted so much time choosing the damn colours of the stupid flowers. The house was completely silent, a note on the counter left to him, Mary and John, explaining that the rest had gone to the Roadhouse a few hours ago and taken Cas with them. Those bastards.

Jo shook her head. "Ah. I see. Lisa was right; you are hung up on the Novak guy. Pity, really. I was hoping that you'd get on with her, but no matter. What do you want me to do with these? Throw them in the trash?" She gestured to the roses.

"No!" Dean almost spat out his beer in an attempt to guard the flowers (he hadn't spent ten dollars on them just to get them thrown in the trash, no matter how overpriced they had been). "I'll just give them to Cas later."

"Why wait? He's right over there if you want to make a move." Dean glanced over his shoulder, following her gaze to where it rested: Sam, Gabriel, Jimmy, Amelia and Cas all sat clustered together in one of the tiny booths that the Roadhouse offered, the table in front of them littered with glasses that had probably once been filled with some kind of alcohol. Cas was in the middle of laughing at something Sam had said, long and loud, his cheeks flushed, his eyes bright, freshly out of the shower. He looked happy, happier than Dean had seen him in a long time. He was about to turn back to his own drink and complain about this fact to Jo, when Cas suddenly stood, saying something about it being his turn to get the next round (to which the rest of the table occupants cheered rather rowdily and Jimmy clapped his brother on the shoulder), and slid out of the booth, stumbling a little, until he regained his balance and made his way over to the bar.

"What can I do for ya, Cas?" Ash greeted him, a smile on his face.

"Five beers, please." Cas shoved a collection of bills across the counter, leaning against it and letting his eyes roam freely as he waited, stopping when he noticed Dean mere metres from where he was standing.

"Hey, Cas," Dean greeted, trying to sound nonchalant in front of the suddenly uptight expression on the other man's face.

"Dean," he replied. "What're you doin' here?" There was a slight slur forming on his words, Dean noticed.

"I just...y'know, came to bring you these." He scrabbled around for the roses, practically shoving them into Cas' chest. "For you, man." Cas eyed them suspiciously and Dean quickly elaborated. "You know, for bein' an ass earlier this week. And, you know, for bein' an ass since December first when you got here. I've been a shitty friend, and I just - Cas?" He frowned. "Cas, why are you laughin'?"

" _Because_." Cas dumped the roses onto the bar counter beside the glasses of beer that were starting to appear. "Y'don't get it, d'you, Dean? Y'don't understand."

"Then help me understand! Make me understand, Cas, because I don't -" He was cut off rather promptly by Cas, who rolled his eyes, grabbed the front of his shirt (the one that he'd changed into recently, because he didn't want to show up looking like a slob) and yanked him forward so that their lips clumsily collided into an alcohol-soaked kiss. It only lasted a few seconds, but it was enough to wipe Dean's mind completely void of...well, anything, really, other than shock.

Cas pulled back rather suddenly, almost sending Dean tumbling off his bar stool. He suddenly seemed a lot more sober, his blue eyes wide, the irises seemingly even bluer around his dilated pupils.

"Cas?" Dean managed. "What -...?"

"M'sorry. I just..." Cas stayed still for another moment, still clutching the front of Dean's shirt in his fists, before dropping his hold on him and turning on his heel, almost sprinting from the Roadhouse, the sound of concern from the others following him, along with Gabriel's indignant cry of, "Hey! Where's my beer?".


	14. December 14th: Gabriel, Dean, Amelia

_**December 14th: Gabriel, Dean, Amelia  
**_

 **Gabriel.**

" _Ughhhh..._ "

"There we go, buddy." Gabriel gave his younger brother a pat on the shoulder, as Cas crouched over the toilet for the third time. "Get it out of your system already." Cas could do nothing but whine wordlessly in response. "Sheesh, I can't believe how terrible you are at holding your liquor once you get well and truly drunk." It took a lot to get Castiel drunk, but once he was, he became rather unstable. Gabriel used to take it upon himself to make sure that Cas didn't go overboard and end up spending his mornings with his head against the toilet seat whilst the older Novak watched on from his perch on the side of the shower, praying that the vomiting would stop by the time that their parents discovered them.

Cas raised his head for a moment to send a death glare his way. "I...hate...you, Gabe," he said weakly, voice cracking, before he returned to his original position, groaning again.

Gabriel shrugged his shoulders, unabashed. "It's not my fault if your body can't handle fun." He gave Cas another tap on the shoulder, less comforting than the last. Cas retched for another few moments, before sitting back on his haunches, breathing heavily and running a hand through his hair.

"Have you see Dean?" He asked once he had gotten his breath back.

"Dean?" Gabriel frowned. "Um, no. Not since yesterday. Why d'you ask? Is this about the kissing thing?"

Cas tilted his head to one side, despite his hungover state. "You saw that?"

"No. He told us - well, okay, he told _Samsquatch_ when he demanded to know what the hell that dumbass had said to upset you, and then he came back to our table and told everyone else. Jimmy looked ready to freaking murder when he realised that Deano hadn't run after you and got down on one knee to beg for your hand in marriage right there and then."

"That sure sounds like Jim."

"I thought I was going to have to break up some kind of fight at some point," Gabriel snorted. "But Deano disappeared soon after in that Impala of his; I assume he crawled in at some point this morning before you woke up to puke everywhere. Or maybe he crashed at Gordon Walker's place or something to avoid seeing you or getting on the wrong end of Jimmy's right fist."

"Hm." Cas shifted on the floor so that he was now sitting properly, drawing his knees up towards his chest. "God, I was so stupid."

"At least you're not like Jimmy and drawn into farmyards when drunk."

"Gabriel, I'm serious."

"So am I."

"Thanks to me, I've ruined any chance I ever had of having a civil relationship with Dean that wasn't full of grudges and regrets."

"Too late for that." Gabriel rolled his eyes heavenwards. "It seems to me that the only relationship that you and Dean can live comfortably with is either one where you viciously hate each other or one where you can't keep your hands off each other." Kind of like right now, the older Novak reasoned, thinking of the drunken kiss Cas had given the elder Winchester.

"I don't viciously hate Dean. I could never viciously hate Dean. Not ever."

"So? What _do_ you feel for Dean, then?"

Cas paused for a moment, thinking about it, but the effort of doing so was obviously too much for him in this state as he let out another high pitched noise of complaint and clutched at his head.

"There there," Gabriel said in response, not sounding all that reassuring. "You look like hell, Cassie. C'mon, up with you. Into bed. I'll grab some stuff from the medicine cabinet to help with the headache. You done puking?"

"Dunno," Cas mumbled, managing to shakily pull himself up and onto his feet, hands pressed against the tiles on the wall for support.

"Hm. Better take a bucket just to be safe." Gabriel reached for the object as he spoke, holding it under one arm and extending the other around his younger brother, helping him limp miserably out of the bathroom and back towards Dean's room. "C'mon, Grandpa. Bed time."

"Mmhm," Cas hummed, his brow creasing as Gabriel yanked back the blankets on Dean's bed and placed the bucket down beside it. "But -"

"No, buts." Gabriel's voice was firm. "You're not lying on the floor in that state. If that ass has a problem with it, he can talk to me about it."

Cas waited another moment, as if trying to muster up the energy to complain, but, in the end, he simply nodded and almost collapsed down onto the bed, curling up on his side as soon as his head hit the pillow, burrowing his nose into the cotton. Gabriel draped the blankets over him again before perching atop the sheets next to his brother, watching as his restlessness ceased and his breathing became deeper and more even. Being an older brother was hard work, Gabriel reasoned, reaching around the side of the bed for something to read whilst he kept watch to make sure that the younger Novak didn't choke on his own vomit.

And if Cas happened to mumble garbled half-sentences about Dean in his slumber, Gabriel simply pretended not to notice.

* * *

 **Dean.**

" _ **He did what?**_ "

Dean winced at the volume of the shriek coming from the woman sat, cross-legged, opposite him. "He kissed me."

Lisa gaped at him, fumbling for her glass of wine. " _Seriously?_ "

"Yes!"

Her expression changed to one of glee; Dean was expecting her to start clapping at any moment. "No way! What kind of kiss was it?"

"What's that supposed to mean?"

"You know! Was it a kiss on the forehead? A peck on the cheek? A smooch on the lips? C'mon, details!"

"On the lips."

"For how long?"

"How the hell am I supposed to know that?"

"You mean you weren't counting?" Lisa tutted. "Dean, this is exactly the sort of thing you should be taking notice of in a situation like yours! Think really hard; how long was it?"

Dean squinted as he thought back to the events of the previous night. "I don't know. Like, six, seven seconds, maybe?"

"That's more than the average, then. That's a good sign." She smirked at him. "Someone definitely likes you."

"If that's the case, why did he run off the first chance he got?"

Lisa waved her hand in a dismissive fashion, almost sending wine sloshing over the side of her glass. "Probably just nerves! Didn't he say anything about it when you went after him?" Dean said nothing in reply to that. "I mean, you did...you did go after him, right? Right?"

"Well..."

"Dean..."

"I mean..."

" _Dean._ Please, for the love of God, tell me that you went after him."

"Not exact - Ow!" Dean massaged his kneecap whilst rolling his eyes. "Jesus Christ, Lisa! What have I done now?"

"How in the hell can you sit here so casually and say that you didn't go after him?" Lisa's eyes were wide and incredulous. "I don't believe that - I can't believe this - What the hell were you thinking?"

"Hey! There was no thinkin' involved in this!"

"Well, maybe there should have been!" Lisa downed half of her glass, before placing it back on the carpet beneath them. "So, what did you do, then?"

"It kinda got a little chaotic after that. Cas ran off, Gabriel was whinin' for his beer, Jimmy was about to come over and punch in in the jaw, Sammy started yellin' at me from across the room and askin' what the hell I'd done -"

"More like what you didn't do," Lisa snorted.  
"Jo was the only one who was really calm in any way. She got Gabe his beer before he threw a bitch fit, and managed to get Ash and Amelia to get a hold on Jimmy before he could murder me there and then."

"I don't blame him."

"Hey! I thought you were supposed to be on my side in all this!"

"Excuse you, I'm not on anyone's _side_! I'm just calling it like I see it! Someone has to; I mean, if it were left down to you, Cas would be married to Meg Masters with five children by now."

"Oh, _God_. Don't even joke about that."

Lisa merely grinned.

* * *

 **Amelia.**

"He's alright," Amelia commented, not bothering to look up from the pages of the book in her lap when she heard the sound of footsteps pausing at the bedroom door. Probably just Jimmy, she reasoned, come to check on his twin yet again. "Just a little unsettled. Sleep's the best thing for him."

"In _my_ bed?"

This made her glance up. That voice certainly wasn't Jimmy's. "Dean. I didn't hear you come home. Where have you been?"

The elder Winchester was leaning against the door, inclining his head towards her but never taking his eyes off the person in his bed. "With a friend. Settin' some things straight."

"Right." She closed the book with a snap, pinching the brink of her nose as she did so. Three hours of sitting in the same spot had taken its toll on her, to say the least.

"He's okay, then?"

"Hm? Oh. Yeah, he's fine. A little hungover, is all." She cast a glance towards Cas, who was snoring softly, drooling on Dean's pillow as he did so, which was both adorable and kind of weird to watch. Amelia had always known Cas as Jimmy's uptight twin brother, who didn't bother with getting emotional; he just always got on with things, and that was the way it always had been. Well, until they'd all decided to spend Christmas in Lawrence, that is. "Hey, can you keep an eye on him for a moment? Just in case he wakes up and needs something? I need to grab a glass of water."

"Yeah. Sure."

"Thanks." She clambered off the bed gratefully, stretching her arms out in front of her as she picked up her empty mug (that once contained fruit tea) and headed for the stairs. She glanced back over her shoulder just before the room vanished from her line of sight. Dean had actually entered the room now, and was sitting on Cas' makeshift bed on the floor, looking at Cas as if he was trying to study his sleeping face and work out some greater meaning that he did not yet understand. When he eventually gave up, he rested his head against the edge of the mattress, eyes shut, seemingly in some kind of deep thought.

"Amelia?" Jimmy's quiet voice sounded next to her on the stairs. "What are you - Oh. Aw." He followed her gaze, watching the scene in the room before him. "That's kind of sweet. What's he doing?"

"I don't know." Her tone gave away her mystification. "I think he's trying to set something straight."

"Doubt that something is his sexuality," Jimmy replied with a muffled snort.


	15. December 15th: Castiel, John

_**December 15: Castiel, John**_

 **Castiel.**

Cas grunted as he rolled over onto his back, wincing at the aching in his neck. Sleeping in the same position for the majority of the day certainly had drawbacks, no matter how comfy it had been at the time.

At least the freaking headache was gone, and something good had come out of letting Gabriel coerce him into sleeping in Dean's bed.

He let his head loll against the pillow, dragging the back of his hands across his eyes as he glanced about the room. He expected to see it completely empty with the door closed, left to his own devices once night had set in, but, to his surprise, the door was still partly open. Dean was sprawled across the floor, he realised a second later, in Cas' makeshift bed, still fully clothed, the blankets pulled up to his chest and caught in one of his fists. His sleeping face looked peaceful, more peaceful than he had seen him in a long while. Cas would have been content to lie in bed for another entire day (and probably several days after that) just so he could observe Dean like this, when his stomach gave a rather loud grumble, petulant after being ignored all of yesterday, which meant that Cas had to heave himself out of the warm bedsheets, stumbling slightly on his shaky legs, and edge his way towards the door in order to avoid waking the elder Winchester. Not that he should of worried; Dean was still as heavy a sleeper as he always had been. Even Cas stubbing his toe on the stairs and hissing out a pain-filled curse of "Oh, _FUCK_ ", didn't rouse him from his slumber.

Sam was leaning against the kitchen table when he eventually made it down to the kitchen, going over something in his paper with John. He grinned when he saw the younger Novak sibling standing in the doorway.

"Mornin', Cas! Back with us?"

"Yes. Well, I think so." He took a seat at the table, as Sam poured him a cup of coffee and passed the mug towards him, which he took gratefully. "Maybe I shouldn't go near another bar any time soon. Or, at least, until after Christmas."

"Just thank your lucky stars it wasn't a farmyard," Sam snorted.

Cas frowned at this as he sipped his drink. "Huh?"

"Ask Jimmy. He'll be able to explain it better than I can." Sam turned back to John. "Is it all okay, though? I need this paper to be the best thing I've ever turned in."

"Seems to be." John drank from his own mug before smiling. "But, then again, you're the expert 'round here, Sammy, so I'm not sure what advice I could offer ya."

Sam shrugged, looking a little uncomfortable. "I wouldn't say _expert_ quite yet. Thanks, though, Dad." He scooped the paper up and filed it safely into his folder, before snapping the ring binder shut. "Say, Cas, why don't you come with me when I go deliver this? It'll get you out of the house for a few hours and into the fresh air. I promise, we won't go anywhere near any bars."

Cas felt his lips twitch up into a smile at Sam's joke. "Well. Doesn't look like I've got anything else to do. Let me just go and take a shower first; I don't think you'd appreciate being seen out in public when I look like death and smell like I've just sampled an entire liquor store." Sam and he shared a small chuckle, before Cas rose from his seat, taking his mug with him as he climbed the stairs towards the bathroom. Dean was still asleep when he slipped back into the room in order to grab some clean clothes, and Cas hoped that it would stay that way. Due to his day of hangover recovery yesterday, he'd avoided all chances he could have had of talking to Dean about what had happened between them at the Roadhouse. Which was just fine with Castiel, because what the hell would he actually say to Dean to explain himself? " _Hey, Dean. Sorry I planted one on you when I was drunk the other day. I never meant to; I just couldn't bear the thought of you giving up on your supposed crush on me and going to dinner with Lisa, because, funnily enough, I maybe, just maybe, might have a crush on you too?_ "

Yeah, he reasoned, as he started the shower and stepped under the water immediately, not even noticing the chilled temperature of the water, that probably wouldn't go down very well. Especially considering that Dean hadn't even wanted Cas to know of his affections towards him, choosing to speak to Jimmy and Sam instead of him.

It appeared that the only option in this scenario was to suck it up and deal with it alone, just as he always had done. He had coped with Dean-related heartbreak before, and it looked like that he had to do it again.

 _Great._

* * *

 **John.**

John watched Cas leave the room with a puzzled expression, before turning to Sam, who was still stood beside him. "Okay, Sammy, what's goin' on?"

"Huh?" Sam's brow creased in confusion. "What are you talking about?"

"Uh hu." He looked unconvinced. "I think y'know what I'm talkin' 'bout. What's goin' on with Cas and Dean? Seems to be so much back an' forth with those two chuckleheads that it's givin' everyone here whiplash."

Sam snorted. "Yeah. You could say that."

"It's got Mary real worried, y'know. Got both of us worried. I don't think any of us want a repeat of what happened last time."

"You're right. None of us want that. But, it's complicated, you know?"

"In what way?" Sam paused for a moment, and John let out a heavy exhale. It really was none of his business, especially now that his children were adults and free to do as they pleased (within reason, of course), but Dean was still his son, and Cas was still one of the Novak kids who had become a part of their family, the one who had held Dean's hand on the way home from school and who had given him his trenchcoat to wear when it was cold out, regardless of whether he needed it himself.

"I know," Sam said, when John voiced this opinion to his younger son. "Believe me, we all feel that way sometimes: caught between not wanting to get involved but, at the same time, feeling that we need to get involved and help them."

John hummed in agreement to this. "I very much doubt it that you and the others chose the not-wantin'-to-get-involved option."

Sam shrugged, looking sheepish. "You got me. We have been having a tendency to interfere with these things rather a lot."

John raised an eyebrow. That response didn't sound too promising. "Define _a lot_."

"Well..." Sam dragged out the word. "We may or may not have accidentally-on-purpose let Cas and Dean overhear us talking about how the other still liked them? And then we may or may not have let them carry on thinking that in the hopes that they'd pull their heads outta their asses and get back together already?"

John shook his head. " _Sammy..._ "

"Yeah, I know, I know. It was kind of a stupid idea. We've already had this discussion multiple times since then. Jimmy's trying to take all the blame for himself. But it seemed full proof at the time, y'know? Nothing could go wrong - but, of course, it did."

"What went wrong?"

"Jo Harvelle tried to hook Dean up with this Lisa chick. They hang out all the time now, so Cas probably thinks that Dean isn't interested in him anymore."

"That's unfortunate." John wasn't a man for showing his emotions all that often, but he was pretty sure that his emotions were visible across his face right now. He really did feel bad for the Novak kid. It had been pretty clear to everyone, John was sure, about how much he still liked Dean. Having to take heartbreak twice must have been hurting him like a bitch.

"Of course -" Sam hesitated for a moment "- it kind of didn't help matters when we took Cas to the Roadhouse the other night, got him drunk, and then watched him plant one on Dean."

Well. _That_ piece of information certainly explained a lot. " _Sam -_ "

"Hey, in our defence, we didn't know that Dean was gonna be there!" Sam held up his hands. "We assumed that he'd be at Lisa's for dinner, not sitting in the Roadhouse with a bunch of flowers!"

"Flowers?" This momentarily sidetracked John. He wasn't sure he had ever heard of Dean buying flowers before.

"Pink roses. For Cas. I think Jo's got hold of them right now - that's not important right now, though."

"You're right in that regard." John took another gulp from his mug. "What's important right now is how you lot're gonna fix what you started."

"I'm not sure we know how," Sam admitted, toying with the folder in his arms.

"I'm sure you'll figure it out, Sammy. You're a smart bunch, despite everythin'." John nodded firmly. "I got faith in you."

"I'm not sure that faith is wise."

"Well. We'll see, won't we?"

* * *

 **Kind of short, I know, but still important! We're gearing up for the last ten chapters now! (There might be some fluff in there somewhere...)**  
 **Writing John's POV here was really hard; I hope I got him right (or, at least, semi-right.)**  
 **Until tomorrow, my little sock puppets XX**


	16. December 16th: Crowley, Gabriel

_**December 16: Crowley, Gabriel**_

 **Crowley.**

This could quite possibly have been the most humiliating and degrading moment of Crowley's life so far. Worse than when his business went sailing out of the window. Worse than when he had to grovel to Bobby. Worse than when he had to make up that ridiculously sappy story about his supposed long lost love from college in order to uphold his side of the bargain with the Novak boys.

No, no, this was far worse. And Winchester wasn't even _trying_ to hide his shit-eating grin as he pretended to carry on working on the Toyota parked in front of him with the hood propped up.

"They look _great_ ," he was saying, barely able to keep his voice even around the laughter caught in his throat. " _Seriously._ You look _stellar_."

Crowley shook his head, causing the bells on the top of his reindeer antlers to jingle merrily, which only made Dean smirk more. "Don't you dare try and demean me about this atrocity, Squirrel. You're not looking any better." He nodded towards Dean's bright orange Christmas sweater, the one that had a rather goofy-looking snowman stitched across the chest.

Dean gave a shrug. "What can I say? Mom made this for me, so I wear it every Christmas. _You_ , on the other hand, got coerced into wearin' those things, thanks to Bobby. I think it's fair to say which of us is the bigger idiot here."

 _You_ , Crowley thought to himself, _for believing that bullcrap story I told you last week._

He rolled his eyes as he spoke aloud. "Fine. Whatever helps you to sleep at night when you curl up in bed all alone. Unless you've actually started asking Castiel Novak to join you there again?"

Dean raised his middle finger towards him. "Mind your own freakin' business. What goes on between me and Cas, King of Hell, is nothin' to do with you."

"Is that a yes, then?" Crowley persisted. Sometimes, he wondered why on earth he was so interested in Squirrel's romantic attachments, specifically Castiel Novak, but then he remembered just how much of a grouchy asshat Dean Winchester could be when his feelings were hurt, and that usually resulted in him sulking in the corner and savagely ripping the head off of anyone who dared to creep over and disturb him.

"It's an " _It's complicated_ "," Dean replied, waving his hand in a vague gesture, glancing back at the car in front of him.

"So, what, he's not currently in your bed, but you _want_ him to be?"

"Yes - I mean, no, no - I mean, yes, he's not currently there, technically, but he's not - "

"I think your babbling speaks for itself, Winchester." Suddenly, the abominable antlers that he had been forced to wear during the build-up to Christmas didn't seem so bad when compared to Dean's crippling relationship status. "C'mon, spill. Some of us are just dying to know what's been happening. How far have you gotten? Have you two even -?"

"I think someone's becomin' a little _too_ invested in this."

"It's only because I care, Squirrel. You are, after all, my work colleague, something that is a big part of my life. Therefore, it could be argued that you are one of the things that complete me. And what kind of best friend would I be if I didn't assess your choice of partner and make sure that they're suitable enough for you?"

"Whoa, whoa, I don't remember anythin' about us bein' best friends!"

"Why shouldn't we be? We both have a lot in common."

Dean folded his arms across his chest, obscuring the view of the snowman on his sweater. "Oh, yeah? Name one thing that we have in common."

Crowley paused for a few minutes, racking his brains for something to reply with. "We're both young, attractive males?"

Dean snorted. "Have you looked in a mirror recently?"

"I thought I was being rather generous with that comment - because, as I'm sure you've realised, not all of us can look as good as I do whilst working in a garage."

"That's debatable, but alright."

"But, anyway, we're getting off topic here. You were going to tell me all about you and Castiel, weren't you?"

"No. I really wasn't. Like I said, what goes on with me and Cas -"

"-Is your own business, yes, I know. No need to repeat all of that rubbish. But I wouldn't be a very good best friend if I didn't investigate into this. Who else is going to pick up the pieces when this ultimately goes wrong yet again?"

"What's that supposed to mean?"

"Winchester, just because you've got your head stuck up your own ass, does not mean that everybody else has. I've watched enough relationships crash and burn in my time, and, if you don't do something sooner rather than later, it appears that you and Mr Novak will head the same way. One of you will move on and leave the other heartbroken. It's the way that it always is with these passionate love affairs."

"S'not an affair. Affair implies that I'm already goin' out with someone else, and clearly I'm not."

"What happened to Lisa Braeden?"

Dean frowned."How'd you know 'bout that?"

Crowley gave a nonchalant shrug of his shoulders. "I have some very...reliable sources."

"Well, then, your "reliable sources" are crap, considering I never really went out with Lisa."

"Oh, yes, that's right." Crowley looked amused. "You're saving yourself for Angel Pants, aren't you?" He chuckled at the silence he received from Dean. "You'd better get a move on, if that's the case. Mr Novak is rather attractive prospect, from what I can tell. Won't be long before someone else besides you notices this; do you really think Angel's gonna wait around for you to get a grip on yourself when that happens?"

"Why don't you just shut your damn mouth, Crowley? You don't understand what's goin' on." Dean fired a glare in his direction, before chucking his spanner into the toolbox beside him now that he realised that his shift was over for the day.

"No." Crowley folded his arms across his chest and shook his head, despite how his antlers jangled. "I think _you're_ the one who doesn't understand what's going on, Winchester."

* * *

 **Gabriel.**

"I wasn't aware that one family needed so many freaking Christmas tree decorations."

Mary leaned over to fondly ruffle Gabriel's mop of blonde hair. "You can never have too many decorations during the festive season, Gabe." Her eyes went back to the tree, humming as she thought. "We need more over here, I think. Cas, honey? When you're done pinning that, be a dear and go and grab me some more tinsel from that box in the kitchen, would you? Gabriel'll help if you can't find any...You're a star." She beamed as Cas nodded, beginning his descent down from the stepladder now that the reels upon reels of streamers were now hanging from the living room ceiling.

"C'mon, little bro." Gabriel rose from his seat on the floor, which was slowly becoming ridden with pinches of glitter and runaway strands of paper chains. Cas picked at the knitted bobbles on his sweater, an action that didn't go unnoticed by his big brother.

"Feeling festive yet?" Gabriel asked, once they were alone in the kitchen.

"Not exactly."

"Seriously? How could you not be in this house? You know May always goes overboard at Christmas. Don't you remember that year when she tried to paper chain the entire house?"

Cas slowly cracked a smile. "I remember. Dean, Sam and I had to find pairs of scissors to cut them all down, and then we felt so bad about it that we made her some new ones, the ones that I just put up through there."

"Christmases here are definitely more exciting than Christmases back home with our Mom and Dad," Gabriel continued. "Over there it was all about Christianity and religion and being thankful. Here it feels more...homely, I guess? More about family than God and the Bible. What about your Christmases in Pontiac?"

"They were nothing big. Jimmy, Amelia and I sit on the couch and watch daytime TV for most of the day whilst eating a lot of sweets before getting drunk once it gets dark." Cas gave a shrug. "To be honest, I'm going to miss doing that this year."

"Why? Because Dean'll be there?"

"No. Well, yes, I guess so, but also no. It's not all about him. It's more about not liking change. I've become so accustomed to our low-budget Christmas in Illinois that I don't want to spend Christmas any other way. It was the same when I left for college. I'd shared nearly every Christmas with you and the Winchesters; spending Christmas just me and Jimmy alone was awful."

"You could have come home."

"After all that happened before we left? I don't think so. Mom and Dad didn't seem to care that we weren't there."

"They did. They just didn't tell you."

"That seems to be a recurring theme in my life."

"What makes you say that, Cassie?"

Cas glanced up, meeting his eyes for a few seconds, almost as if he was planning to say something; the sound of the front door slamming behind him cut him off. He pressed his lips together as Dean entered the kitchen, unceremoniously kicking off his boots as he went.

"Dude," Gabriel complained. Dean merely grunted in response, heading straight for the coffee pot.

Cas cleared his throat. "I think I'm gonna take this through to Mary; she can pick whatever tinsel she wants, then." He grabbed the box off the table and backed out of the room as hastily as he could.

Gabriel sighed. Honestly. Cas was like a deer in the headlights, ready to crap himself if the wrong person - namely, Dean - got too close.

"Gabe?" The sound of Dean's voice made him jump.

"Yeah?"

The elder Winchester leant against the counter. "Would you be able to talk to Cas about somethin' for me?"

"What?"

"I want to know if he's still losin' sleep over that whole kiss business."

"Why can't you ask him yourself?"

"Because every time I walk in the same room as him, he does that. Makes some stupid excuse and then leaves." Dean let out a sigh. "I don't know. Probably readin' into it too much. Just, could ya have a word with him? Please?"

"Sure thing?" It sounded more like another question than a response, but it seemed good enough for Dean.

"Thanks, man. I owe you one."

"Yeah. Don't get used to it."


	17. December 17th: Dean, Castiel

_**December 17th: Dean, Castiel**_

 **Dean.**

"Thanks for doing this, Dean. I owe you one."

"Nah. Don't think anythin' of it, Sammy." Dean rounded another corner, pulling the Impala into the first available lot space he saw. "Bobby's cool with it an' I'll make up my hours tomorrow." He cut the engine before turning to his younger brother. "What was so important that you needed me to come shoppin' with you?"

Sam gave a shrug. "Emergency Christmas present run. I still haven't bought anything for Gabriel...or Castiel, for that matter." He sent his brother a reproachful look.

Dean sighed, pushing his door open as a way of response. "Yeah," he said after a moment. "Me neither. Guess I'd better get on that, huh?"

"Hey, speaking of which..." Sam slammed the passenger door and then followed a few paces behind his older brother as they made their way towards the shopping mall, joining the sea of people that flowed in and out of the building, burdened with the weight of shopping bags. "What's up with you and Cas?"

"I wish I knew myself so I could tell you, Sammy. It's...it's complicated, y'know? Did it ever feel like that with Gabe?"

Sam blinked, obviously surprised that Dean, of all people, would bring complicated feelings into the conversation. "At first, yeah. I wasn't sure if he liked me, you know, like that. I thought I was just being stupid, so I kept quiet for ages. Why on earth would he want to be in a relationship with someone who had barely started school by the time that he was a teenager?"

"Because you're my brother," Dean replied loyally, his tone firm and absolute. "And also because you're freakin' awesome, Sammy."

"I know _you_ think that -"

"And I'm right to think that."

"- but I didn't know that Gabe thought that."

"He would be an idiot not to." Dean gave Sam a playful jab in the ribs, making the younger Winchester smile.

"Thanks, Dean. But it all worked out in the end. And I'm fairly certain that it will for you and Cas too."

"Well, I don't know about that. It's kind of hard to know what to do around Cas sometimes. He'll either be actin' like he likes me and there's no one else in the whole damn world that he'd be with, and then he goes and ignores me for days on end!" He threw his hands up in frustration as he spoke, nearly clipping another shopper around the head.

"Still thinking about that kiss, huh?"

"What do you think? Of course I am. Pretty hard not to think about how your ex might have yet another possible crush on you."

"Well, that in itself is a good sign, right? It takes a lot of balls to be able to do something like that, so he wouldn't have kissed you if he didn't really like you, and that's true whether Cas is drunk or sober."

"Yeah, but he hasn't spoken to me since then! It's been, what, three days, give or take? And every time that I walk into a goddamn room, he makes some bullshit excuse and runs off as fast as he can!" The hurt in his voice is obvious, even to him. Sam's expression was sympathetic.

"You still really like him, don't you?"

"Yeah." Dean kept his eyes trained on the floor beneath their boots as they headed towards a vintage bookstore. "Guess so. Not that it matters now."

"What do you mean? Of course it matters! There's still every chance that -"

"I don't know, Sammy. I think I've just missed my chance. Again. When I didn't run after him after that stupid kiss and make out with him there and then."

"Considering that Cas puked about an hour later, you should probably be glad that you didn't make out with him and end up with him vomiting over you."

"I wouldn't have minded."

"Yes, you would. You would have thrown a bitch fit, Dean, and you know that you would've."

"Okay, fine, maybe I would've complained a little bit, but I would've taken care o' him too. I would've sat with him all day and watched over him to make sure that he had everythin' that he needed. I would have gone all out, Sammy. Done all of that chick-flick shit. Wouldn't even have complained 'bout it."

"Wow." Sam raised an eyebrow. "Must be love if you're willing to go through all that."

"Yeah. Guess it must be."

* * *

 **Castiel.**

Gabriel hummed in appreciation as he took a bite of the cheesecake slice on the plate in front of him."Been a while since we spent some quality time together, eh, little brother?"

"Hm," Cas murmured in agreement, picking at his own food. He had been perfectly content to sit in the Winchesters' living room and read his latest book on the couch, but, no, since Sam and Dean had headed out for the afternoon, Gabriel had decided that today was the ideal day to drag Cas away from his reading and encourage him to be out in public - because, obviously, Cas clearly hadn't embarrassed himself in public enough times during the course of this month already.

"So, how are things with you, Cassie?" Gabriel licked his fork clean before spearing his cake again. "You and Deano sorted everything out?"

"Not exactly."

"That means, no, then." His older brother let out a sigh. "What's up? Are you still thinking about that whole drunken kiss business?"

"Of course I'm still thinking about it! I made such a fool out of myself, and now Dean doesn't want anything to do with me."

"Really? Are you sure about that? Have you any evidence to support this claim?"

Cas hesitated for a moment. "Well - No, but -"

"Whereas I, on the other hand, know for a fact that Dean asked me to talk to you about this entire mess, since you won't actually speak to him."

"He did?"

"Yup. He asked me to ask you whether you were losing sleep over the kiss business." Gabriel popped another mouthful between his teeth and chewed. "So? Are you?"

Cas shrugged. "Not exactly."

"So, yes, then."

"No!"

"No?"

"Yes. No. Oh, I don't know!" Cas resisted the urge to throw his arms up in the air, and instead settled for slumping back in his seat and dragging a hand down the length of his face. "It's complicated."

"That's what they all say, Cassie," Gabriel declared. "So, what's the problem? Do you regret the kiss?"

"No!" Cas said instantly. "Of course not. It was...well, aside from the being drunk part, it was a nice kiss. But then -" He paused.

"What?"

"Nothing."

"No, come on, you can't just tease me like that. Spill it. It doesn't matter what it is, or how corny you sound. Have you heard me talk about my Samwich?"

"I was gonna say, all my kisses with Dean are nice." Cas felt himself going almost as red as the festive tablecloth underneath their plates. Gabriel chortled.

"That is actually adorable."

"Shut up, Gabe. It doesn't matter anyway."

"What's that supposed to mean? Of course it matters. Your feelings matter, Cas, even the ridiculous ones like your insane infatuation with Deano that he somehow returns."

"He won't want to return them anymore. Not after that night at the Roadhouse and how much of a douche I was to him before that." He slumped against the table, head in his hands. "Maybe...Maybe I've just lost my chance."

* * *

 **Kinda sad ending to this chapter, I guess, what with both of our babies feeling like they've lost their opportunity to be together. But, don't worry! The next will be happier; we're going to bring the fluff back in droves over the next few days as we get closer and closer to the big day! X**


	18. December 18th: Castiel, Mary

_**December 18: Castiel, Mary**_

 **Castiel.**

"Are you _sure_ about this?"

"It's only following a recipe, Jimmy." Cas placed the bag of sugar down on the counter, along with the large mixing bowl that he had managed to find tucked away in one of the cabinets. "How hard can it be?"

"Um..." Jimmy looked incredibly worried for someone who wasn't even baking. "Very? Y'know, if you're _you_."

"I've come a long way since that unfortunate episode in Pontiac, Jim. You should have a little more faith in me."

"I've tried, Cas, believe me, but not even your outstanding microwave creations can make up for when I had to stand out in the cold wearing only my underwear."

"I've apologised for that multiple times."

"And yet here we are." Jimmy rolled his eyes as he tugged his jacket on over his shoulders. "What are you trying to bake anyway?"

"Pie," Castiel replied, pushing the cookbook across the table so that his twin could see. "I thought it might be nice for everyone when they get back. I'm trying to make an effort to be more festive."

"Huh! Good luck with that! Why don't you just come out to dinner with us? Mary and John might start to get offended if you keep running off all the time."

"I'm sure they'll cope after they see my cookery skills."

"Surely you mean _lack of_ cookery skills."

Cas grabbed one of the apples from the box beside him and aimed it at his brother; Jimmy ducked out of the way and it hit the floor, rolling away relatively unscathed. "Get out of my kitchen if you can't be supportive, Jimmy."

"With pleasure." Jimmy gave him a two-finger wave as he sauntered out of the room. "I don't particularly want to be inside when you manage to blow the house up."

"Piss off!" Cas yelled at his retreating back.

"Gladly!" Jimmy called back, before Gabriel shoved him out of the front door, rolling his eyes and throwing a "Bye, Cassie!" over his shoulder as he slammed the door behind them, plunging the house into peace and quiet. Cas heaved a sigh of relief at this, and turned back to his recipe book, consulting the list of ingredients. It was only following a recipe. How hard could it be?

He had just finished putting the dough into the refrigerator and beginning to clean up (after his first three attempts), when he heard the door opening and closing again as someone trudged through the hallway.

"Hey, Jimmy," Cas called out, not bothering to look up from the kitchen counter. "Didn't think you'd be back so early. Don't you dare come in here; the pie's not even ready."

"Since I'm not Jimmy, can I still come in?"

Cas' head snapped up. "Dean?"

Dean tugged his hat off his head and ran a hand through his dark blonde hair. "The one and only."

"What are you - I thought you were at work - "

"I was. But Bobby and Crowley were havin' some kind of domestic row, so I slipped off early to get away from it all." Dean shrugged his coat off as he moved further into the kitchen. "What are you doin'?"

"Baking." Cas kept his eyes trained on the scraps of dough in front of him, left over from his many failed pie experiments. "Apple pie. It was supposed to be a surprise for everyone when they got back from dinner."

"Didn't you want to go to dinner too?"

"Not particularly. I needed to the peace and quiet. Plus, baking relaxes me somewhat, even if I'm pretty terrible at it."

"You don't seem to be doin' such a bad job." Dean had walked to stand beside him, watching what his hands were doing. "But, hey, why don't I offer you a hand?"

"Really?"

"Yeah, sure. My kitchen skills are to be admired, after all."

"Oh, I see." Cas glanced at him out of the corner of his eye. "So you've moved on from cheese on toast and soup, then?"

"Hey! I was just gettin' into the ropes, alright? A man has to start somewhere!" They shared a chuckle, before Dean let out a quiet sigh. "Cas...Look, about the kiss -"

"Dean, I know. It was stupid of me. I'm sorry. It wasn't fair for me to put you in a position where you felt uncomfortable. That was something that I never wanted to do."

"Cas -"

"Dean." Only now did Cas look up properly, his blue gaze locked into Dean's green eyes. "I don't want to talk about it. Please. Can we just put this behind us?"

Dean opened his mouth to say something, possibly to argue, but he paused, and after a moment, he sighed again. "Alright. Whatever you want. We'll forget 'bout it, yeah?"

"Yeah. Thank you." Cas turned back to the bowl in front of him, but, for some reason, his chest didn't feel any lighter. A weight of sadness still hung over him.

 _Because you like Dean_ , a little voice whispered in the back of his head.

 _Shut up!_

"I didn't say anythin'!"

"What?" It was a few seconds before Cas realised that he had actually spoken aloud. "Oh, no, not - I didn't mean you - I was just talking to myself - Never mind."

"Hey, man. Nothin' wrong with talkin' to yourself. S'not like I haven't seen ya do it before." Dean gave his shoulder a playful nudge as he began gathering the right ingredients for the filling. "Cas?"

"Hm?"

"When this is done...what d'you say we watch a movie or somethin'? The others won't be back for a while yet, and it'd be a shame not to utilise the silence now that Gabe and Sam aren't here to make out in front of us."

A movie. Cas could handle a movie, right? A movie was a fun pastime - a platonic pastime, yes?

"Okay. Sounds good. Only, not _Pulp Fiction_. Jimmy's watched that movie far too much for someone in the festive season."

Dean laughed, the sound loud and long and happy, something Cas hadn't heard from him in a while. It made his stomach do all those funny twists and turns again."Sure. No _Pulp Fiction_. Gotcha."

* * *

 **Mary.**

"Jimmy, I really think you should come inside now..." Mary folded her arms. "You'll get a chill, and I'm not sending you back to Pontiac sick."

"After Cas has been cooking? I don't think so." Jimmy peered through the front door fearfully. "He's done something. I can feel it. Probably released some kind of killer gas in there."

"Hey! Sweet!" Gabriel's voice echoed from inside the kitchen. "Who made the pie?"

"Wait, wait - there's actually pie?" Jimmy's eyebrows quirked up, and he ducked through the door, stepping into the warm house, the threat of killer gas evidently forgotten. "Cas made a pie? A real pie? Not some kind of deadly war pie?"

"You're the pie expert, Jimmy," Sam snorted. "You tell us."

Mary rolled her eyes fondly at the chatter coming from the kitchen, turning around in order to seek out her husband; John was leaning up against the living room door frame, watching something in the room whilst trying to conceal a grin.

"John?"

"Shh." He beckoned towards her, keeping his voice quiet. "Come and take a look." Mary frowned a little in confusion and followed him to the doorway, the confusion fading in favour of a brilliant grin when she saw the sight. Dean and Cas were curled up on the couch, feet on the coffee table. The younger Novak's head was leaning on her son's shoulder, whilst Dean's head was resting on the crown of his, his nose buried in soft strands of dark hair.

Mary had to force herself not to break out into some kind of giddy laughter. "They look so nice together!" She whispered to her husband.  
"Yeah." John slung an arm around her shoulders. "They do."

"We have to savour this. Hold on..." She fumbled in her pocket and brought out her phone, snapping a picture of the sleeping pair, before grinning at John.

"What was that for?"

"Proof. For my future grandchildren."


	19. December 19th: Sam, Gabriel, Castiel

_**December 19th: Sam, Gabriel, Castiel**_

 **Sam.**

Sam rolled his eyes at the expression on Cas' face as he climbed out of the Impala. "I'm not sure that this is a good idea."

"Don't worry about it, Cassie!" Gabriel slung an arm over his shoulder and made a sweeping gesture to the crowded ice skating rink in front of them with his free hand. "Everyone goes skating at this time of year. You'll love it, trust me."

"Somehow, your words aren't reassuring me."

"Oh, you're just being a grumpy guts!" Gabriel complained. "C'mon!" He grabbed Castiel's hand and dragged him off, rather unwillingly, in the direction of the stalls where the skates were kept.

"Was this really such a bright idea, Sammy?" Dean asked, as they trailed along at least twenty paces behind the two Novaks.

"Sure." Sam gave a shrug. "The leaflet says that it's supposed to be a family activity, so it can't be too bad. Besides, it'll give us a chance to get out of the house and get away from all the tension that's been hanging around during the last few days...or weeks." He sent Dean a reproachful look. "Jerk."

"Bitch," Dean shot back, before switching to another topic of conversation."Where's Jimmy? I thought he was all for ice skatin' today."

Sam resisted the urge to roll his eyes. Dean could try all he liked to be subtle, but it wasn't working. He could see through his older brother immediately, and no way was he going to get out of talking about this. "He was. But Amelia's caught some kind of throat infection, and he's insisting that he stay by her side at every moment, waking or sleeping. Why?" He allowed his smirk to cross his face. "Were you worried that he'd make comments about you and Cas and your little cuddling session yesterday?"

"Shut up." Dean's gaze flickered over to where Cas was, almost being wrestled into his skates by Gabriel, who apparently wouldn't sleep easy until he had forced his little brother out on the ice, before his eyes returned to Sam. "I was asleep and out of it, man. How was I supposed to know what my body was doin'?"

"Have you and Cas even mentioned it?"

"Nope. And I'd like it to stay that way."

Sam bumped their shoulders together. "Hey, man. Maybe you should talk about it? Talking never hurt anyone, after all."

"I tried to. It's Cas who doesn't want to talk, and I'm not gonna discuss it if he don't want to."

"Dean -"

" _Sammy._ " Dean cut him off sharply. "Just drop it. Please."

"Come _on_ , Samwich!" Gabriel yelled, drawing their attention over to him; he had his hand clamped down on Cas' shoulder, as if there was a chance that the younger Novak would try to make a run for it. "Let's pick this up a little!"

Sam let out a sigh, regarding the terrified expression on Cas' face. This was going to be a long afternoon; he could feel it already.

* * *

 **Gabriel.**

Gabriel drew to a stop beside his fiancée, skidding a little on the ice. "Aren't those two just the cutest thing you've ever seen, Samsquatch? Look at them!"

Sam glanced across the rink to where both of their brothers were standing. Cas was clinging on to the railing that surrounded the rink, a look of fear in his eyes, whilst Dean skated backwards, trying to get him to let go, it appeared, going by the hand gestures he was making and the silent _Are you crazy?_ look Cas was giving him.

"They are pretty cute," he said aloud, agreeing with Gabriel's statement. "But they won't even talk to each other! Cas is uncomfortable or something -"

"They're stubborn, Samwich. Think about it. This isn't as bad as them hating each other and indirectly ruining our Christmas with their lust-filled feud."

"Suppose so." Sam linked their fingers together as they sailed around the ice once more. "But what if we were wrong to interfere in the first place?"

"What makes you say that?"

"Something Dad said the other day. About finishing what we started."

"Samsquatch, I think you're reading too much into this. We did a good thing." Gabriel swung their hands as they skated. "Perhaps it didn't run as smoothly as it could have done, but it's all working out, don't you think?" He nodded over his shoulder towards their brothers. Sam followed the gesture, watching as Cas slowly, hesitantly, let go of the rail. He wobbled dangerously for a few seconds, before the ground slid out from under him and he went down, tumbling towards the ground. Dean's arms darted out to catch him, but the sudden weight in his grasp made him stumble, and he too slipped, letting out a cry as he took them both down, landing directly on top of the younger Novak and almost knocking their foreheads together.

Gabriel let out a shriek, almost losing his balance too as he let go of Sam's hand to clap wildly. "Priceless!" He chortled. That was the thing about hanging out with Cas. There was never a lack of entertainment.

* * *

 **Castiel.**

"No." Cas fixed Dean with a steely glare, tightening his grip on the railing.

"C'mon, Cas, just let go!" Dean grinned at him, effortlessly keeping his balance as he travelled backwards and Castiel edged after him. "It'll be fine! See, I'm doin' it!"

"You are experienced in ice skating. I, on the other hand, am not."

"What, didn't you go skatin' in Pontiac?"

"Jimmy tried to get me to go with him and Amelia multiple times. I refused every invite, and this is why." He moved to gesture around the ice rink with one hand before realising that this would require letting go. And that was to be avoided at all costs.

"Please, Cas!" Dean's green eyes pleaded with him as he spoke. "Nothin' will happen. It's easy! C'mon!"

Cas scowled at him for a few more moments, before he let out a heavy exhale and started to relax his grip, prising his fingers away from the rail one by one, until he had let go completely.

"I'm doing it!"

Dean's face lit up. "Atta-boy, Cas! I knew that you could!"

The victory grin on Cas' face was short-lived, however; all of the energy he had directed into focusing on Dean and his smile had caused him to lose balance. Cas felt his legs give out under him, and suddenly the ground of the ice rink was swooping up to meet his face.

"Cas! -" Dean's arm grabbed hold of him, but he clearly couldn't hold himself upright with Cas hanging off him, and before Cas really realised what was going on, he was sprawled across the cold surface beneath him, Dean directly on top of him, face mere inches away from his, their breath mingling together in the air.

Did Dean always have this many freckles?

"Hey! Chuckleheads!" Cas dragged his eyes away from Dean's face above him to see Gabriel and Sam gliding towards them. "You gonna just lie there or are you actually gonna make out?"

Dean fired a glare at his future brother-in-law's words. "Shut the hell up." He pulled himself up almost immediately, holding out a hand that Cas gratefully accepted.

Sam raised his eyebrow at their interlocked fingers. "If I were you guys, I'd keep doing that. This place is getting crazy busy; doesn't take much to slip over." He grasped Gabriel's hand too as he spoke.

"Sam!" Dean hissed, glowering at his younger brother. Cas was about to protest too, but he felt himself about to start slipping again, and he tightened his grip on Dean's hand, nodding.

"That sounds wise."

Sam sent Dean a look, winking as he did so. "See? He thinks it's _wise_."

"Bitch," Dean retorted, before sliding forward across the ice, head held high, taking Cas with him. "Those two are idjits."

"Yeah," Cas agreed, giving Dean's warm fingers a slight squeeze as they rounded a corner. "They are."


	20. December 20th: Castiel, Amelia

_**December 20: Castiel, Amelia**_

 **Castiel.**

"Hey, Cas! Cas! _Castiel!_ "

Cas let out a muffled groan, marginally raising his head from the pillow and squinting against the dull light of the early morning.

"Wha' is it?" He mumbled, voice still heavy and rough with disuse during the night.

"Snow!" Dean was leaning over the side of his own bed, perched on his knees and grinning at him like a child on Christmas morning.

"Sn-...Huh?" Cas dragged a hand down the length of his face, his brow creasing in confusion.

"It's been snowin', doofus!" Dean rolled his eyes at Cas' sleepy bewilderment. "Come and see!" He reached over and grasped Cas by the wrist, tugging until the Novak let out another grumbling sound and sat up, glancing out of the window. Sure enough, the heavens had opened during the night hours, and now a thick white blanket of frozen droplets now covered every available area in sight. "Isn't it great?"

"Yeah. Terrific." Cas stifled another yawn that was threatening to rise up out of his mouth. "Did you seriously wake me up just to show me this?"

"Nope! Well, yeah, but no." Dean had clambered off his bed by this point, and was in the process of retrieving his jacket from where it had been ungraciously slung across the floor the night before and shrugging it on over the top of his pyjamas. "We're goin' out in it."

"What, now? Right now? At -" Cas checked the neon numbers on the alarm clock on Dean's bedside table "- seven AM?"

"Oh, come on, don't look like that!" Dean chortled quietly, as he bent down to pull his boots on. "Where's your sense of fun gone, Cas?"

"It's in bed," Cas quipped dryly. "Asleep. Which is exactly where I should be right now."

"So, what, you're gonna make me go out there on my own?" Dean pushed out his bottom lip in an attempt to recreate Sam's puppy dog face, the one that Castiel had seen him use on Gabriel many times when he needed him to do something. It always worked on Gabe, and it looked like it was about to start working on another Novak too. Dammit.

"I didn't say that." Cas let out a sigh, stretching his fingers over to where his suitcase was and dragging his trenchcoat towards him, copying the elder Winchester and pulling it on over his pyjamas. "You're the worst," he said, in response to Dean's victorious grin.

"And yet, here we are anyway."

"Hm." Cas mustered up some kind of smirk. "Not until I turn my ass around and go back to Pontiac and file for emotional abuse."

"You wouldn't dare."

"I'm a tax accountant, Dean. I know about this stuff."

"I'll get Sammy to defend me."

"How do you know he won't take my side?"

"I'm his brother."

"But Gabriel is my brother, and Sam's fiancée. Knowing Gabe, he would manage to persuade Sam to side in my favour using his... _charm_."

Dean thought this over for a moment, and then shuddered. "Yeah. Alright. Mental images that I really didn't want, Cas. Remind me to never get into a court of law with you."

"Noted." Cas tied his shoelaces and rose to his feet, wincing as he stretched. "Now, since you insisted on this endeavour, are you actually dragging me outside into the cold or not?"

"Someone's eager all of a sudden," Dean remarked, keeping his voice hushed as they moved out of the room and across the landing, trying not to rouse anyone else.

"I wouldn't call it eager," Cas whispered in reply, as they made it down the stairs without any incidents. "More like kidnapped and unwilling."

Dean let out a quiet chuckle, rescuing the back door key off the hook in the hallway, along with two long scarves, knitted by Mary in days long ago. He looped one of them around Cas' neck. "There. You're gonna need that once we get outside."

" _Great_ ," Cas replied, without much enthusiasm, thinking fondly of the warm bed he had left upstairs in Dean's room - or, even better, his flat back in Illinois, where nobody else lived besides him, which meant that it was perfectly acceptable for him to put his socked feet up on the radiators when the winter chill got too much and not expect judgement.

Dean was right. He definitely did need the scarf once they had stepped outside into the Winchesters' back garden. Cas suppressed a shiver, and bundled the knitted material tighter around his neck, tucking it inside his trenchcoat to try and keep it in place.

"Now what?" He asked, sounding grumpier than he intended to as he watched Dean practically dance through the snow like he was seven years old once more.

"I don't know." He smirked. "You wanna build a snowman?"

"I don't know whether you're being serious or joking."

"I'm bein' serious! C'mon, it'll be like when we were kids again! We had fun makin' them, didn't we?" He started kicking the patch of snow at his feet, beginning to roll it into the right shape for the body.

"Yeah," Cas pointed out, scooping up a ball of snow for the head and adding to it until it was bigger than his palm. "That was in 1998, Dean."

"Still less than twenty years ago."

"Not by much."

"Cas!" Dean threw his hands up in exasperation. "Stop bein' so...freakin' grouchy!" He grabbed the snowball at his feet and hurled it at the other man, catching Cas by surprise as the frozen water hit him square in the face and began to melt instantly, dripping down his neck and seeping into the scarf.

"What -?" His mouth twitched into a smirk. "Oh, you've started something now, Dean."

"Bring it!" Dean was already racing up the garden, trying to reload on snow as Cas grabbed a lump of the stuff and hurled it at his retreating back, catching him in the shoulder. "Oh, it's freakin' _on_ , Novak."

* * *

 **Amelia.**

Amelia found herself being dragged into consciousness by the faint sound of laughter echoing up through the guest bedroom window. She cracked open an eye, letting out a noise of complaint at the interruption, glancing over at Jimmy, who was still asleep beside her and snoring lightly.

Wincing at the stiffness in her muscles from being bedridden all day yesterday, she heaved herself out of the warmth of the four blankets she had wrapped herself up in, padding across the carpet and peering through a gap in the curtains, smiling at what she saw down below her through the glass. Cas and Dean were chasing each other around the back garden, hurling snowballs at each other and giggling like five year olds every time their weapons hit their intended targets.

" _You can't ignore a truce, assbutt!_ " Cas was yelling.

" _Watch me, short-bus!_ " Dean replied, seizing another snowball and throwing it; Cas ducked quickly.

" _You're gonna have to try harder than that, Winchester!_ "

" _Oh, it's on!_ "

Amelia grinned to herself, letting the curtain fall from her grasp as she inched her way back towards the bed, where the promise of warm feet was waiting.

Maybe things on this vacation were finally starting to look up.


	21. December 21st: Dean

_**December 21st: Dean**_

 **Dean.**

"This, right here, is why I hate Christmas." Dean let out a grumbling noise to accompany his words, as he glared down at the potatoes in the shopping cart like they had wronged him in some way.

Cas rolled his eyes as he walked alongside his friend, heading out of the grocery store and towards the Impala. "You always were a drama queen come Christmas time."

"Am not!" Dean protested, giving the cart a kick for good measure, maybe to show just how much of a drama queen he _wasn't_. (Because he totally wasn't, okay?) "I just don't see why we had to leave this stuff 'til the last freakin' minute. We've had practically a month to sort this out."

"Sometimes it just gets on top of you," Cas replied, sounding rather absentminded as they braved the later December chill that was whirling around the parking lot. Thank Christ they'd found a spot close to the entrance; Dean wasn't sure that his toes would have survived if they'd had to search the lot for the Impala.

"Hm," Dean replied, suddenly having rather inappropriately-timed flashbacks to the ice rink incident that weekend when he found himself sprawled on top of Cas. He would be lying if he said that he hadn't given it a second thought over the past two days that had since followed - like, he would be lying a lot. But, what could he do? Cas had already made it perfectly clear that he had no interest in discussing anything to do with that stupid kiss that night at the Roadhouse, and it seemed that anything remotely related to romance was off the cards too.

Well, it could have been worse. A lot worse. It wasn't like Dean was unused to heartache at the hands of Castiel Novak and his pretty blue eyes. Not that he'd ever say that in public, and certainly not when Cas was in earshot. He didn't want to creep the guy out even more than he already had done during the duration of this vacation, after all.

Cas, however, wasn't even paying him that much attention. He was focused on something at the other end of the lot, where something of a small crowd had gathered, the sound of music and clapping drifting over to the spot where the Impala was stationed.

"What's going on over there?" He nodded with his chin in the direction of his gaze.

"Hm?" Dean's eyes followed the same path as Cas', not really all that interested in what was going on all the way over there, especially when home was a short, few-minute drive away and filled with cosy socks and hot coco."Oh. No idea. Probably some kind of charity thing, what with it bein' Christmas an' all."

 _Charity_ appeared to have been the wrong term to use; Cas' eyes lit up with a newly kindled interest. "We should go check it out."

Dean snorted. "Uh, no, we shouldn't. I don't particularly want to - Cas! Hey! Where are you - Come back!" Cas had taken off, not having listened to his reply, practically sprinting across the parking lot in order to see just what this "charity thing" was really about. Dean stared after him for a few seconds - they still had bags of groceries to unload into the back seat, and he still wanted to get home - but eventually, he sighed loudly, slammed the Impala door, and raced off after his friend for fear of losing him in amongst the crowd of last-minute Christmas shoppers that swarmed all over the place.

"Cas!" It took him a few minutes to catch up with the Novak, finding him gathered with the rest of the group that they had been observing from their spot by the car. "What are you doin'?"

"Listening to them play." Cas nodded towards the three-piece band in front of them, his foot tapping along the frosty ground in time to the beat of the song that they were performing. "They're from the animal sanctuary, apparently. They want to attract new volunteers."

Dean resisted the urge to let out a groan. Cas had always had some kind of fascination with animals. There was absolutely no chance that he'd be able to drag him away now for at least another twenty minutes. He folded his arms, hugging himself to try and conserve what little body heat he had stored up from being inside the grocery store (which had been lit like a furnace). Cas didn't seem bothered at all by the cold; the only thing that he seemed interested in was the board displaying cute pictures of puppies and kittens that stood behind the band, things that would not keep Dean occupied for the long length of time that he knew he would be standing out in the cold for. Thank God there hadn't been bees on that board too, or Cas would have never been dragged away until it was nightfall and the grocery store manager threw him out.

Dean shivered again. How the hell would he not die from hypothermia in these conditions?

"Hey, Cas." He nudged the other man in the side. "Let's help 'em out a bit. Drum up some audience."

"What do you mean?" Cas finally dragged his eyes away from the animals, only to frown at Dean in confusion.

"Like this." Dean grabbed the hand closest to him and pulled him in, wrapping the other arm around his middle and shuffling backwards, practically dragging Cas along as he stumbled and lost his footing. "Dance with me."

"Are you serious?"

"Deadly serious."

"In public?" Cas raised an eyebrow. "I didn't think that you went for this sort of stuff."

"It's Christmas, isn't it? The season of givin'. I can sacrifice a little for the animals."

Cas caught his balance and began to follow his lead, letting Dean step back and forth and spin them around a few times. "How generous of you," he snorted, trying to avoid the looks they were getting for the shoppers who had began to gather around them.

"I'm a generous man, Cas."

"I remember."

"You'd better." Dean was silent for a moment, before swallowing. "Hey...Cas?"  
"Yes?"

"I know you didn't really wanna talk 'bout it, but that business at the Roadhouse a couple o'weeks ago."

"Dean -"

"No, no. Let me just say this, okay? Then we never have to bring it up again, if you don't want to."

Cas nodded after a brief, half second pause. "Alright. Carry on."

"Thing is...that kiss...it, well..."

"It...?" Cas prompted.

"Well, it got me thinkin'. 'Bout a lot of stuff."

"What sort of stuff?"

"You. Me. You _and_ me. That sort of stuff."

Awareness dawned in the pair of bright blue eyes. "Oh. You mean...that sort of stuff?"

"Look, Cas - You don't have to say anythin' right now - I was just thinkin'-...I know that there's a lot of bad water under the bridge and all that...Basically-" He cut himself off with a huff of frustration. This shouldn't have been so difficult. Dammit, they've already gone through this whole awkward process once. "Thing is, Cas...I was wondering if, like, perhaps, you might wanna go on a -" He was silenced for a second time by a sudden noise of surprise from Cas, who had stepped on a patch of heavy frost, left over from the snow the previous day. His foot slid, causing him to almost lose his balance again, his body starting to fall backwards towards the concrete.

"Whoa!" Dean, thankfully, still had his balance this time, tightening his arm around the other man and bringing him back up, so that their faces were level again, almost as if it was some kind of elaborate waltz move. "You okay?"

"Yeah," Cas replied, although he sounded a little breathless. "Fine." He glanced out of the corner of his eye towards the shoppers still crowded around them, some clapping, one cat-calling in the background. Not that Dean could blame them. To someone who hadn't had the full view of what had just happened, it was probably so easy to get the wrong idea.

 _Except that you were just about to try and ask your ex out again,_ the little voice that sounded like Sammy reminded him again. _Well done, Dean._

"Dean?"

"Hm?"

"I said, do you want to start heading home?"

"Home?" He repeated, probably looking as dazed as he realised that he sounded.

"Yeah." Cas raised an eyebrow. "Preferably before we both skid over again. I don't want a repeat of what happened on Saturday."

 _But I might._

"Sure." Dean dropped his grip on him after making sure that he wouldn't slip over again, rubbing the back of his neck.

Dammit. He'd been so close. Now he had to start this whole process of getting the courage to ask Cas all over again.

But...

Tomorrow was always another day, right?


	22. December 22nd: Jimmy, Castiel

_**Today was gonna be slightly different, but then I got inspired by a photo-set on Pinterest! I don**_ _ **'t know where the link is, but it's floating around the Internet somewhere. It sounded so much like Jimmy speaking that a couple of lines are included here (to an extent).**_

* * *

 _ **December 22nd: Jimmy, Castiel**_

 **Jimmy.**

"Hey...Jim?"

Jimmy glanced up from the bowl of ice cream that he was currently devouring to look towards Dean, who was slouched against the kitchen counter. "Yeah?"

"How did...?" Dean trailed off with a sigh, before taking a long swig of beer and starting his sentence again. "How did you, y'know, ask Amelia out? For the first time?"

Jimmy's brow creased in confusion. "That's a weird question."

"Yeah, yeah, I know. I just - I need advice."

"And you thought I was the best possible choice?" Jimmy raised an eyebrow.

"Well, I can't exactly go to Sammy 'bout this. And there's no way in hell or heaven that I'm goin' to Gabe 'bout it. You were the next best option."

"Boy, you really know how to make a guy feel special, don't you?" The Novak let out a snort, before shrugging. "To answer your question, I don't really know. It just sort of happened. One day, I just saw her and thought, " _Today's the day_ ". And I just...asked. I guess you gotta get to the I don't give a fuck phase before you can ask. Why?"

"No reason. Just wonderin'."

Jimmy's eyes narrowed. "I don't buy that for a goddamn second, Winchester. C'mon, what is it? You trying to ask some poor innocent girl out to dinner? Not that Lisa Braeden chick again, is it?" This was just what he _didn't_ need. Not when the Destiel pie was just starting to come together after seven long years simmering in the oven.

"Not...exactly." Dean shuffled. "Somethin' like that. But, anyway -" He carried on before Jimmy could open his mouth to try and make another guess as to why Dean was suddenly so interested in his dating life "- What should I do? Got any advice?"

Jimmy rolled his eyes elaborately. "I don't know, man. Just...follow your heart, or something. I'm not an expert on your love life."

"Yeah, but...I don't know what my heart's tellin' me to do." Dean drained the last of his drink, and moved across the room to dispose of the bottle in the garbage can and rummage around in the refrigerator for another beer. "What do you think it's tellin' me?"

"How the hell should I know? I'm not your freaking heart, am I?"

"Well, no, but that's not the point I'm tryin' to make."

"You don't seem to making _any_ point, Dean."

"Yeah, well, this stuff's hard, okay?"

"You still haven't told me what this _stuff_ is all about."

"It's complicated."

"Now you just sound like my brother when he's trying to avoid a conversation. Come on, it can't be that complicated. We've all been there, after all."

"I just need some advice. There's this great... _person_ who I've been thinkin' 'bout askin' out for a while. Just I have no idea how to go 'bout it."

"See? That's all you had to say." Jimmy rolled his eyes. How on earth Cas had managed to put up with this guy, he had no clue. "Well, for starters, what does this _special person_ like, in terms of dinner? Always good to know if you're planning to take them out somewhere."

Dean thought for a moment, giving Jimmy odd looks as he did so. "Uh...they like lots of stuff. Like, they like healthy stuff, but they're not like Sammy who dies a little inside every time he sees somethin' over a certain amount of calories. Y'know, they're not fussy."

"Wow. So helpful."

"Hey, man, I'm tryin' my best here!" Dean pouted around the neck of his beer bottle as he took a drink. "It's difficult, alright? I haven't done this in a while."

"I didn't expect you to take have taken your drunken hookups out to dinner," Jimmy quipped. Dean looked confused at this, and he elaborated. "Sam and Gabriel. They told me."

"Oh, _great_. Just what I needed."

 _Yeah, that makes two of us._

"Okay, so you've been decidedly unhelpful about what this person likes in terms of food. What's their favourite food?"

"Don't know."

"How long have you known them?"

"A while."

"How _descriptive_. Might need a little more to go on."

"Fine. I've known them for years now. A _long_ while. Happy now?"

"Not really -" _Because you haven't confessed your undying love to my brother_ "- but it'll have to do. So, you've known them for years. How exactly do you not know their favourite food by now?"

"It might have changed since I last asked. I don't know."

"Don't really seem to know a lot, do you?"

"Hey, look, man, this is hard enough as it is, without your sarcasm stinkin' up the place!"

"I wasn't aware that sarcasm let off any kind of smell."

Dean stuck his tongue out at him. "Assbutt."

"Asshat," Jimmy shot back. "Now, was that it? 'Cause I was gonna go and find a movie to watch whilst I finish wrapping Christmas presents."

"No!" Dean took a step forward, as if he was going to try and block Jimmy's path out of the room.

"Alright, sheesh. Take the chill train, why don't you?" Jimmy sat himself back down in his seat.

"C'mon, man, you gotta know somethin'."

"I know lots of somethings, Dean."

"Oh, yeah? Like what?"

"Well..." Jimmy pretended to deliberate for a moment, before snorting. "My name is Jimmy Novak, I was born in Lawrence, Kansas, and you're a freaking idiot, Dean Winchester."

"I didn't mean _any_ kind of somethin'."

"You should have been more specific, then."

"You're an ass, you know that?"

"I have been told that on many occasions." Jimmy merely flashed a smile at him. "What somethings do you want to know about? First nugget of wisdom is free, the next ones will cost you."

"Cost? You never said anythin' 'bout cost?"

"Just practising good business, Dean. A sales provider for AM radio has to perfect these things."

"I'm not payin' you to find out stuff that I could just Google for myself."

"Who said anything about it being money? I was only gonna ask you about some stuff of my own. Like who this _special person_ is."

"I'm not tellin' you that."

"That implies to me that I know this person." At Dean's silence, Jimmy grinned. "Ah. So I do know this person."

"I'm still not sayin' anythin'."

"Your reluctance and defensive tone tells me that it's someone close to me who I might have some comments about. Can't be Amelia, because you've known her for less than a month and have barely spoken to her. Can't be Lisa, because you've known her even less than that. Can't be Gabriel, because you've been close to murdering him in the past. Which means that the only people left are myself, and -"

 _Oh._

"- Cassie!"

"What?"

"It's Cas, isn't it?" Jimmy let out a mirthful chuckle and clapped his hands eagerly. "I can't believe this - This is the most adorable thing I've ever witnessed."

"Shut up, dude." Dean shifted, trying to distract from the red that was currently climbing its way up his neck and towards his cheeks. "You make it sound like we're a couple o'fluffy rabbits or somethin'."

"You may as well be." Seemed like the Destiel pie was coming along nicely. He should have never doubted his cooking skills. "Well, what the hell are you still doing down here? Get out there and ask him!"

"Really? Just like that?"

"Why? What's the matter now?"

"I just -...Are you sure? I mean, with all the stuff that happened last time..."

"Dean." Jimmy had gotten out of his seat again and moved to dump his bowl in the sink, turning on the faucet to rinse it out. "Believe me, I haven't forgotten what you did. It's kind of hard to forget when someone makes your twin brother break down in your arms. But, hey, I'm a man of forgiveness, and, if you make Cas happy - and I know that you do -, then I wish the pair of you well. Hell, I can even dust off that best man speech I started preparing at one point and spruce that up a bit if it would make you guys feel better."

Dean's shoulders visibly relaxed. "Thanks, man. That, y'know, means a lot -"

" _However._ " Jimmy turned back to face him. "If you ever, and I mean _ever_ , hurt Cassie again, I will not hesitate to hunt you down to the ends of the earth, rip your spleen out through your nose, and then take a shower in your spinal fluid to celebrate my revenge. Understand?"

"Understand what?" Castiel's voice echoed from the doorway, making them both turn around. Jimmy smirked suddenly.

 _This should be entertaining._

* * *

 **Castiel.**

"Understand what?" Cas leant against the kitchen door frame as he spoke. Dean swallowed, his posture tensing up at the sight of him. Something told him that he wasn't supposed to have walked in on this conversation. "Oh. I interrupted you, didn't I? Sorry, I can come back -"

"No!" Jimmy cut him off, a grin on his face. "Stay. Join the fun, right, Dean?"

"Shut up." Dean fired a glare at the other Novak twin before turning back to Cas. "Hey, Cas, can I ask you somethin'?"

"Is this the same something that you were going to ask me yesterday?"

"Yeah. Listen, I was wonderin' - If you wanted - Maybe you and I could...go out to dinner tomorrow?...Not - Y'know, not like _that_ , or anythin' - But...kinda like _that_?" Dean winced at his own words. "That was a crap explanation. Let me try again -"

"Are you...?" Cas cut him off, speaking slowly to try and de-construct his garbled words. This wasn't what he thought it was, was it? "Are you asking me out on a date?"

"No!" Dean said instantly. Jimmy gave a loud cough."I mean...yeah. Yeah. I am." Cas' twin brother snorted in the background, causing the Winchester to turn and glare at him again. "Somethin' to contribute, assbutt?"

"Nope. Just enjoying myself."

"Yeah, well, freakin' enjoy yourself somewhere else."

"And miss this? I don't think so." He gave Cas a thumbs up, as Dean returned his gaze to him.

"So...what do you think, Cas? How 'bout it? You, me, dinner, fun?"

"Just as eloquent as ever," Jimmy muttered. Dean exhaled sharply; Cas was pretty sure that Jimmy would find himself tackled to the ground if he didn't stop.

"Yes."

This distracted Dean entirely. "Wh -...Really?"

Cas offered up a smile. "Yeah. _Really_."

"Hallel-freaking-ujah," Jimmy muttered. " _Finally._ "


	23. December 23rd: Castiel, Jimmy

_**December 23: Castiel, Jimmy**_

 **Castiel.**

Cas plucked a handful of fries from the bowl in front of him, ducking one in the smudge of ketchup on his plate and popping it into his mouth. "I'm glad you chose this place. This is nice."

Dean smiled at him from the chair opposite him, mimicking his actions with his own food. "Thought you'd like it."

Cas nodded, eyes flickering briefly around the 1950s diner and the other couples who were deep in conversation with their partners, before they looked back to Dean. "So, what's going on?"

"What do you mean?"

"You know what I mean. Why did you ask me to dinner?" And why go to _Jimmy_ , of all people?

Dean swallowed his mouthful and then sighed. "Cas, a lot of stuff has happened over the last month or so. I didn't think I was ever gonna see my little brother get married, but Gabe got down on one knee and now I am. I didn't think I was ever gonna see you again, but I have. I didn't think...I didn't think a lot of stuff would happen, and yet it has." Apparently Cas still looked confused, because Dean made a gesture towards him. "Cas, do you ever think 'bout...that day?"

"What day?"

"You know. The day you got your college letter. Before you left for Pontiac."

"Oh. _That_ day." Cas chewed another one of his fries. "I was wondering when that was going to come up. Yes, I think about it sometimes." Probably more than he should have done, actually. "Do you think about it?"

"I did all the time, at first. Just after you were gone, it was the only thing I ever thought about. I was lonely. Then I was just pissed - both at you and myself. And, then, for a long while, I just...didn't think about it anymore. Or, at least, tried not to. I thought 'bout everythin' and anythin' else I could. Did a damn good job of it too. Almost convinced myself at times that it hadn't ever happened. Just some bad dream or somethin'. But then Sammy and Gabe dragged you and Jim back here, and I couldn't forget 'bout it then. I know. Stupid, right?"

"That's not stupid, Dean. That's a natural human way of coping with things."

"So you say," Dean grumbled, taking a long sip of his milkshake, before reaching for some more of the fries. "But it doesn't feel like that. It's part of the reason why I was such a shitty person towards you, always avoidin' you an' stuff. I was pissed that you made me remember, not just how mad I was at you, but also how mad I was at me, for bein' so crappy when you needed me to happy for you."

Cas rested his chin in his palm as he listened. "You hurt me, you know," he said slowly. "But I think you already know that."

"I kinda got the hint when Jimmy came round that day and charged through the house yellin' 'bout how I should prepare for the end." A bitter half smile appeared on Dean's face at the memory. " _I know what you did, Dean, you ass! I know you broke my brother's heart! Get out here right now before I break your fuckin' door down with an axe and punch the livin' shit out of you!_ " He shook his head. "He was _pissed_. He even threatened to start smashin' up Baby if I didn't go talk to him."

"He came home pretty angry too," Cas recalled. "He was kicking the door frame until Mom had to yell at him to stop. And then he just sat in the corner and simmered for the rest of that day. I was almost afraid to go near him, but he came to find me later. Gave me a hug and told me just how sorry he was, and how he would have saved me so much hurt if he hadn't locked us in that stationary closet."

"Did you ever talk about it after that?"

"After we left? No. Mainly because I noticed how guilty it made Jimmy feel, and I didn't want to make him feel worse, and so I kept it to myself. It only came up in conversation once, during a game of Truth or Dare. They asked me when the best kiss I'd ever had was."

"Oh?" Dean grinned. "Which was?"

"Prom," Cas answered, matter-of-factly, biting the straw in his milkshake glass. "During the final slow dance. Remember?"

"Yup. I remember. I kept tryin' to get you to follow me into the bathroom so that we could make out, and you repeatedly told me that it was unsanitary, and that Gabriel and his girlfriend of that week - Anna, wasn't it? - already had the same idea."

"You didn't particularly want to go in there after I told you that." They shared a chuckle, before Dean sighed.

"What have we been doin' all this time, Cas?"

"Being idiots."

"Too right." He stirred his drink, licking the froth from the straw when he had finished. "You think...?"

"What?"

"You think...y'know, that we could ever...try again? Not like jump straight back in like the last seven years never happened, that's not what I mean." Cas had opened his mouth to speak, but after Dean elaborated, he closed it again, motioning for him to continue. "We're not the same people we were back then, yeah? I mean, like, maybe, for the rest of the time that you're here - how long are you here for?"

"A few more weeks yet. My manager said that I could take of as much time as I wanted, considering that I'd never taken a day off since I started working for the firm. _Call it a Christmas present_ , she said. I think it was because she was having Health and Safety inspectors in, and it was safer to get me out of the way."

"Right. Well, I was just thinkin', during the next few weeks, we could...do this again? Like, go out for dinner a few times, take it slow, y'know?"

Cas looked down at his plate, but the smile on his face was obvious, he was sure of it. "Yes. I'd like that."

"Well, then." Dean's expression matched his own. "That settles it, then. Awesome."

"Yeah," Cas echoed. "Awesome."

* * *

 **Jimmy.**

"So?" Jimmy demanded as soon as his twin brother walked into the kitchen.

"So?" Cas repeated with a smile. "So, what?"

"You know what! What happened? Where did you go? What did you say? What did Dean say?" Jimmy's palm slammed on the counter. "Details. Now, please."

Cas smirked. _That freaking tease_. "We went to the fifties diner in the centre of town and had dinner. We talked about what happened between us all those years ago, and we've agreed to try for a second dinner a couple of days after Christmas. Happy?"

"Extremely!" Jimmy clapped his hands in delight. "Ah, I always knew that you guys were meant to be!"

"Did you come to this realisation before or after you threatened to chop Dean's bedroom door down with an axe?"

"Oh, ha ha. You're freaking hilarious, assbutt." Jimmy stuck his tongue out at him, gesturing in his direction with the breadstick he was currently eating. "Look, you're my twin, okay? When someone messes with you like that, they may as well be messing with me. If the roles were reversed, you would have done the exact same thing, and you know it."

"True," Cas agreed with a shrug. "I would have."

"Well, then." Jimmy rolled his eyes. "So, what else happened? C'mon, I want details. Did you kiss?"

"No!"

"Oh." _Well, that was anti-climactic._ "Did you hold hands?"

Cas shifted. "Maybe."

"Ooh!" Jimmy chortled. " _Castiel and Dean, Sittin' in a tree, H-o-l-d-ing hands..._ "

"Shut up!" Cas grinned at him, the words lacking bite, when his phone vibrating in his trenchcoat; he fished it out and answered it, not even bothering to check the caller ID. Jimmy raised an eyebrow. His brother must have been in a good mood.

"Hello?" His voice was still light, almost giddy, when he spoke into the receiver. "Hester! How are you?" He listened for a few moments. "Oh. Why? What's up?" Jimmy watched as his expression began to falter. "Go on...What? What - No! You said -" More pauses. "Hes -" The phone buzzed as someone else spoke at the other end. Cas' smile had slipped entirely by this time, and he pinched the brink of his nose between his fingertips. "I - Fine. Fine. When you put it like that." The person on the other end of the line spoke again. "Yes. Well, a lot of good that's going to do me." He hung up sharply, letting the phone drop down onto the kitchen table as he let out a loud " _Shit_ " through gritted teeth.

"Cassie?" Jimmy ventured. "Who was that?"

It was a few moments before Cas answered him. "That was my boss. Hester."

"What did she want?"

"Me. Back to work. She says that they're understaffed and they need me in as soon as possible."

"When?"

"Monday."

" _Monday?_ This Monday?" Jimmy stared at him. "You're kidding!"

"Is this the face of a man who is kidding, Jimmy?" Cas let out a harsh exhale. "She said that if I chose to just take my holiday anyway, then there wouldn't be a job waiting for me when I got back to Pontiac."

"She can't do that!"

"I don't think she really cares whether she can or not. Point is, she has. Oh, God, what do I do? How do I tell everyone that I'll be gone by Sunday afternoon? How do I tell _Dean_ that I'll be gone by Sunday afternoon?"

"We'll be gone by Sunday afternoon," Jimmy corrected. "I'm coming back with you too."

"You don't have to do that."

"Don't care." His voice was firm. "Where you go, I go. That's what family is for." He moved across the room and wrapped his arms around Cas, pulling him into a tight hug. "I'm sorry. Do you want me to tell Dean for you?"

"No." Cas leaned back sharply. "No. I'll tell him. Just...not yet? I know, I know, that's bad, but I just...I just want to pretend for a few more hours. Is that a crime?"

 _It is when considering what happened last time_ , Jimmy thought.

"No," he said out loud. "Of course not. That's normal. No more shall be said about it, for tonight, at least. Now, I'm about to watch _Pulp Fiction_ again - it's my thinking movie, and you look like you need to do some thinking too. You want popcorn?"

* * *

 **What** **'s this? Has this Moose finally caught up on the days she missed? Yes, she has! Whoo! (Streamers and balloons every-freaking-where). Finally, we are back on track, all set to finish on Christmas Day!**

 **The 1950s diner is a mention to my undying love for T &S. I'll never not read some T&S.**

 **Until tomorrow, the penultimate chapter, my little sock puppets! X**


	24. December 24th: Dean, Sam, Castiel

**Penultimate chapter is here! Let** **'s see what's going down! As Carmilla would say, "Buckle up, creampuffs!"**

 **Also, we just hit 100 reviews! I just...I literally can't even! Thank you so much! You've all just made my entire Christmas :) X**

* * *

 _ **December 24: Dean, Sam, Castiel**_

 **Dean.**

"Hey, Lisa!"

"Dean!" Lisa's cheerful tone echoed out of the receiver of the cordless phone pressed to Dean's ear. "Merry Christmas!"

"A little early, aren't you?"

"Please. Ben's been singing _Jingle Bells_ ever since yesterday - haven't you, love?" She addressed someone else in the room, chuckling as her son spoke in the background. "Yeah, our house is pretty much the epitome of Christmas spirit right now."

"Don't let my brother-in-law hear you say that," Dean joked. "He'll be prepared to fight you for that title."

"Bring it on, I say! But I take it that's not why you called. What's up? How's things with Cas? Please tell me that you haven't done something stupid again."

"So little faith in me, Braeden." Dean rolled his eyes, grinning as he did so, even if she couldn't see him doing it. "Actually, if you really wanna know -"

"Yes. I do."

"You don't even know what I'm gonna say."

"Don't care. I want to know anyway."

"I was gonna say that Cas and I are doin' very well, thanks."

"Ooh!" He could hear the smile that accompanied her noise of excitement. "That's great! Took you freaking long enough, Dean. I always knew that you guys were meant to be together. So, come on, tell me everything. How many dates have you been on? Have you kissed? Made out? Have you -?"

"Whoa, whoa, calm down! I think you're gettin' a little ahead of yourself there, Lisa."

"There is no getting ahead of oneself in these situations, Dean. Stop trying to avoid the question. That's just sending me the idea that you and Cas have gotten down and dirty already."

"You wish. You just want braggin' rights for forever, don't you?"

"Guilty," Lisa replied, unabashed. "So, have you?"

"No, we haven't. We've just been out for dinner, an' that's all."

"Taking it slow, huh?"

"Yeah. Real slow."

"Never thought I'd see the day."

"Hey, I can be a gentleman when I wanna be. I want to do this right, y'know? Not like last time, when I screwed everythin' up. I'm gonna do this properly: dates, kiss on the cheek goodnight, _then_ kiss on the lips goodnight, before the whole distance."

"Wow. That's some dedication. I'm impressed. And also freaking overjoyed for you. Jo is too. She's expecting a wedding invitation any day now."

Dean smirked mirthfully. "I'll make sure that she's first on the guest list."

* * *

 **Sam.**

" _SO, HERE IT IS, MERRY CHRISTMAS, EVERYBODY'S HAVIN' FUN -_ "

"Gabe!" Sam gave his fiancée a shove, grinning. "Calm yourself. It ain't Christmas just yet."

"In three hours it will be, Samsquatch!" Gabriel pecked a soft kiss on his cheek, before practically skipping around the kitchen table throw his arms around Jimmy. "You're excited, right, Jimmy?"

"Hm, yeah." Was all he got in reply.

"Why the long face, Jim-Jim?" Gabriel squeezed his shoulders tightly. "It's Christmas Eve! Santa Claus is coming to mother freakin' town tonight! You should be celebrating, drinking mulled wine, decking the halls with holy, y'know, all of that crap! Not skulking about in here looking like your pet hamster just got shot."

"Just got a lot of stuff to think about."

"Like?" Sam prompted. It wasn't like Jimmy to be so down in the dumps; usually, he was one sugar cube away from bouncing off the walls like a little puppy, never without a smile. "C'mon, whatever it is, it can't be that bad, right?"

Jimmy hesitated for a moment.

"Jim-Bob." Gabriel gave him another squeeze. "You know that we're gonna get it out of you one way or another. It would be safer for everyone involved if you just told us what's up."

The younger Novak glanced between the two of them, before sighing. "Alright. Fine. But, you can't say anything to anyone else, understand? This is on pain of death, okay?"

"Scouts honour, Jim-Jim."

"Too bad you were never a Scout."

"I was!"

"Yeah. For about half an hour. Until they kicked you out."

"Why? What did you do?" Sam enquired with a grin.

Gabriel, for once, looked a little uncomfortable. "Nothing! Well, nothing story-worthy, anyway. But we're not talking about my dalliance in the Scouts. We're talking about Jimmy and why he's being a misery guts on this day of festivity and cheer." He looked expectantly towards his younger brother. "C'mon, spill. It's only a couple of hours until Santa arrives and we all have to be in bed by then." He threw a wink in Sam's direction. "Not necessarily sleeping, though."

"Gabe!" Sam shifted, pretty sure that his cheeks were flushing as he aimed a shove at his fiancee.

"Do you guys want me to leave you alone or something?" Jimmy asked with a raised eyebrow. "I'm pretty sure I could go join Amelia and find something to read."

"Nuh uh. Not until you tell us what's up." Gabriel narrowed his eyes. "Don't make me fight it out of you."

"Okay, okay." Jimmy glanced over their shoulders, before lowering his voice. "Yesterday, Cas' boss called him."

"So?"

"So? She wants Cas back at work - by Monday!"

" _Monday?_ " Gabriel all but screeched, causing Jimmy to whack him on the arm and shush him.

"Shut the hell up!"

"Can she legally do that?" Sam asked, ignoring Gabriel's pout.

"I don't know. But she has." Jimmy let out a frustrated huff. "Bitch."

"Amen to that." Gabriel had moved to the kitchen cabinet and pulled out a bottle of wine; not bothering to fetch a glass, he uncorked it and knocked it back, letting out a grunt at the burn of alcohol in his throat.

"When are you driving back?"

"Sunday." Jimmy took the offered bottle from Gabriel, wiping the neck with his sleeve and downing some of the red liquid inside. "Cas didn't want to miss Christmas with you guys." Sam didn't miss the silent addition of " _With Dean_ " at the end of that sentence.

"Are you leaving too?" He asked aloud. "Or is Cas going alone?"

"Cas is leavin'?"

 _Oh,_ _ **shit**_ _._ Sam winced as he turned around to face the sight of his brother standing in the doorway, the cordless phone still in his hand.

"Dean -" Jimmy began, but this just seemed to make things worse. "Dean, you weren't - Dean, wait!" He barged past Gabriel and hurried after the elder Winchester, who was already striding up the stairs, two at a time. "Dean, it's not what you think - Dean!"

"Fuck." Gabriel broke the sudden silence in the kitchen and rested a hand of Sam's shoulder. "I think shit is about to, uh, hit the fan, huh, Samsquatch?"

* * *

 **Castiel.**

"Hester -" Cas sighed into the phone again. "I know, this is probably my fifth voicemail, but, _please_ , just pick up. If there's any way - any way at all - that you can reconsider this, then I'm begging you to do so. I'll never take another holiday ever again, and I'll work overtime hours for free - whatever you want. Just...please. Call me back." He hung up with a sigh, dropping the phone onto Dean's beside table as he folded another shirt and tucked it into his suitcase. All afternoon, he had been trying to get his boss on the phone, ready to beg in order to get her to reconsider, but it had gone straight to voicemail every single time as the offices were closed for Christmas. _Nice for some_ , he thought bitterly, kicking the suitcase for good measure (and regretting it instantly when the flares of pain shot through his toe).

The door swung open suddenly and banged against the wall, causing him to start. "What - Dean? What are you -?"

"Is it true?" Dean folded his arms across his chest, just as Jimmy also burst into the room, concern splashed across his face. "Are you leavin'?"

Cas' eyes flickered to Jimmy. "You told him?"

"Not on purpose!" His twin protested. "I was gonna wait until you were ready!" He glanced between Castiel and Dean. "I'm just gonna leave you guys alone to talk, okay? Don't do anything drastic." He cleared his throat, quickly backing out of the room and shutting the door behind him with a soft click, plunging it into near total darkness, save for the soft amber glow of the bedside lamp.

"So." Dean said into the silence. "S'true, then."

Cas sighed. "My boss called me yesterday. Said that she wanted me back for Monday, or I'd lose my job. She said that there was nothing else that she could do. I'm sorry."

"Were you even gonna tell me? Or were you just gonna...flit off back to Illinois without sayin' goodbye?"

"Of course I was going to tell you. I just didn't want to make Christmas uncomfortable. I know that this is the worst possible time for this to happen - but it won't be forever, okay? We can keep in contact, and I'll come back and visit."

"Yeah. That's just what you said last time." Cas had to stop himself from flinching at the hurt in Dean's tone. "And then I didn't see or hear from you for seven years."

"Dean -"

"How long are we gonna make it this time, Cas? How long are you gonna be gone? Fourteen years? Or are we gonna make it an even twenty?"

"Stop it!" Cas folded his arms across his chest, mimicking Dean's posture, his eyes narrowed. "This has nothing to do with last time! Last time you told me that you never wanted to see me again! This time, it's different! It's out of my control this time!"

"You still wanted to leave!"

"For God's sake, Dean, I thought we'd gotten past this! I wanted to go _college_ ; I never wanted to leave _you_!"

"Then, why the hell didn't you pick up the damn phone and call every once in a freakin' while?"

"After you told me to never contact you again? I don't think so!"

"Yeah, well, maybe I was lyin'! Maybe I secretly wanted you to call so I wouldn't have to walk 'round racked with guilt every damn day!"

Cas threw his hands up in the air before letting them fall to his sides. "You _secretly_ wanted? What am I, a mind reader?"

"No! You were my boyfriend!"

"And you were mine! You were supposed to be there for me when I needed you the most!"

"Yeah, well, I'm sorry!"

"Yeah, well, I forgive you!"

There was silence for a few moments after that, as Dean processed what had just been said and Cas mentally face-palmed when he thought about how much of an idiot he'd been. All these years, he'd held on to the anger he'd initially felt towards Dean, and now it was suddenly just...gone. Just like that, as if it was nothing more than breath on a mirror that had been wiped away as soon as he had announced his forgiveness.

Before he knew it, Cas surged forward, closing the small gap between him and Dean and crushed their lips together, just as he had done in the Roadhouse, catching Dean by surprise before he threw himself into it, pulling him closer so that their bodies were now flush against each other.

"I love you," Dean mumbled against his mouth. "I love you. I love you. I love you."

"I love you too." Cas pulled back marginally, letting his forehead rest against Dean's, huffing out a breathless laugh. "So much for going slowly this time around, though. I notice that plan went out the window." Dean chuckled too, leaning back in to kiss him again.

"Spend the night with me," he breathed. Cas let out an amused snort, eyebrow raised, and Dean let out another chuckle."Not like _that_ , Cas. Sheesh. Get your mind outta the gutter. I just meant, stay with me. Nothin' unsavoury." His arms moved to wind around Cas' middle, letting his head rest on his chest as if to demonstrate what he actually meant. "Just like this."

Cas hummed contentedly, nuzzling into the fabric of Dean's shirt, wrapping his own arms around Dean neck, fingers anchoring themselves into the material. "Yes, Dean. I'll stay with you."

* * *

 **Holy Jesus Cow on a bike, that got rather sappy towards the end. But I'm a sucker for Destiel cuddles and couldn't help myself! They're just too cute!**

 **Until tomorrow, my little sock puppets! Have yourselves a merry Christmas Eve! X**


	25. December 25th: Gabriel, Dean, Mary, Cas

**MERRY CHRISTMAS, MY LITTLE SOCK PUPPETS! x**

* * *

 _ **December 25: Gabriel, Dean, Mary, Castiel**_

 **Gabriel.**

" _ **IT'S CHRISTMAS!**_ "

"What the -?" Jimmy let out a muffled noise of complaint, squinting as he lifted his head out from underneath the pillow. " _Gabe!_ " He aimed a kick in the intruder's direction. "Piss off!"

Gabriel beamed at his younger brother, sitting at the bottom of the bed with his legs crossed, bouncing as he spoke and rousing Amelia from her slumber too. "Cheer up, Jim-Bob! It's Christmas morning! No one's allowed to be grumpy on Christmas morning!" He tugged at the duvet like an excited five year old. "C'mon! Sammy's already downstairs getting some coffee on the go, and Mama and Papa Winchester are preparing the presents!"

"Oh, _hooray_ ," Jimmy replied, without enthusiasm, which earned him a shove from the bottom of the bed and caused his legs to slide out from under the warm duvet, his feet hitting the floor with a gentle thud. " _Fuck_. It's cold."

"It's called winter, Jimmy." Gabriel gave him another shove, almost sending his brother's entire body onto the floor. "Now, come on, up! We'll start without you if you don't get a move on!"

Jimmy waited for another few seconds, before he let out a groan and pulled himself into a sitting position, rubbing the sleep from his eyes as he did so. "Okay, okay, fine, I'm up."

"Great!" Gabriel leapt off the bed, beaming widely. "I'm gonna go get whoever's still alive out of Cassie and Deano and then it's time for presents!"

"Wha'?" Jimmy blinked, obviously still asleep. "Cas an - Gabe, I really don't think that's a good idea -!"

Gabriel rolled his eyes, bounding out of the room anyway, practically dancing across the landing as he neared Dean's room. He hadn't heard any noises coming from the room since his brother-in-law had gone crashing in yesterday evening, so either they had sorted it out or both of them were dead by now.

Whatever had happened, it was sure to liven up Christmas.

"Cassie?" Gabriel gave a light tap on the closed door, pausing for a moment to listen for any sounds of movement. "Cas? You still alive in there?" Receiving no answer, the older Novak pushed down on the door handle and let the door open ever so slowly in an attempt to make as little noise as possible. "Castiel?" He peered around the door, before he stopped, a shit-eating grin breaking out over his face as he took in the scene in front of him. Dean and Cas were curled up on Dean's bed, atop the duvet, using Cas' trenchcoat as a makeshift blanket; Dean and all of his limbs were wrapped around Cas like he was some kind of human pillow, whilst the younger Novak had his face buried in the head of dark blonde hair, the material of Dean's shirt caught in his fist, almost like some kind of comforter.

Gabriel stayed watching them for a few more minutes, enjoying the looks of contentment on both of their faces, ones that had been seven years in the making, not having the heart to wake them. He shook his head - _daft idjits_ , he thought to himself - before he quietly backed out of the room and shut the door once more, smirking to himself as he turned to go down the stairs.

All's well that ends well, as Sam had once said, and, in Gabriel's mind, this Destiel pie malarkey had ended incredibly well.

* * *

 **Dean.**

Someone was singing.

It was faint, and far away, but it was there alright, pulling Dean out of sleep and back into consciousness, back to the real world, back to the warm body huddled underneath him, getting louder and louder with every moment that passed, until the sound of it reverberated from somewhere close to his ear.

" _I don't want a lot for Christmas_ _..._ _There is just one thing I need_ _..._ "

His mouth pulled up into a smile and he burrowed closer, nuzzling into the fabric of the other person's shirt.  
" _I don't care about the presents_ _,_ _Underneath the Christmas tree_ _..."_ Fingers began to card through his hair in time to the soft singing. _"_ _I just want you for my own_ _,_ _More than you could ever know_ _..._ _Make my wish come true_ _..."_ _  
_Dean shifted his head slightly so that he could join in with the last line. _"_ _All I want for Christmas is you_ _..._ Jesus Christ, you are a freakin' sap, Cas."

A chuckle came from somewhere close by his shoulder. "I learnt from the best."

"Assbutt."

"Hey. That's my line."

Dean smirked, raising his head marginally so that he could look Cas in the eye, nudging his nose against his chin. "Hi there."

Cas' blue eyes twinkled as he smiled. "Hello, Dean."

"What time is it?"

"Uh..." Cas unwound one of the arms from around Dean's shoulders and stretched his fingertips across to the bedside table, managing to retrieve his phone. "Just gone eight thirty. Gabriel texted me an hour ago...said that we look cute sleeping together like this. Looks like you can't hide much in the Winchester house."

"You mean you've only just realised that?"

"What can I say? I'm an oblivious idiot." Cas placed a gentle kiss on Dean's forehead. "Guess the others must be downstairs already." He let the phone drop onto the bed covers. "What do you think? Should we venture out into the real world just yet?"

Dean pretended to consider for a moment. "Nah. They've managed this long without us. They can take another twenty minutes."

"Agreed." Cas returned his arm to its original position. "Agreed wholeheartedly."

* * *

 **Mary.**

"There you are!" Mary clapped her hands when she noticed her eldest son finally shuffling into the living room at eleven AM, dragging a rather bedraggled-looking Castiel Novak behind him, their fingers tightly intertwined. "I was just about to send Sammy up there to make sure that you were still alive!"

Sam looked rather put out by this. "Why would I have to be the one who interrupts whatever they've been doing up there?"

"S'not like you don't know from experience, Samsquatch," Gabriel commented from the other side of the room, causing Jimmy to choke on his glass of whiskey and Sam to grab the nearest item - the pair of fluffy socks Dean had gotten him - and hurl them in his fiancée's direction.

Dean grimaced. "Seriously, you guys are so dirty minded. We weren't doin' anythin' unsavoury, right, Bumblebee?" He squeezed Cas' hand as he spoke; both him and Mary smiled at the use of his old pet name. Adorable habits die hard, after all.

"Well," Mary began, not really wanting to interrupt the moment. "Since you're both here, I guess we should hand out your presents now."

"Yeah." Amelia rummaged around the pile of presents still sitting under the Christmas tree, passing the smallest one over to Dean. "This one's from Jimmy, Sam, Gabe, and I. You'll understand when you open it."

"Oh?" Dean quirked his eyebrow up, tearing at the wrapping paper with his free hand, letting out a snort when he saw what it was. "Mistletoe. Haha. You guys are freakin' hilarious." He sent a sideways glance at the Novak sibling next to him. "How 'bout it, Cas? Audience demand and all that."

"Like you even have to ask." Cas rolled his eyes, stretching up on his tiptoes and bumping his nose gently against Dean's before pressing their lips together, amongst the cheers and catcalls that came from the others in the room, none of them louder than Mary's delighted cries at the happiness etched across her son's face that didn't appear to be shifting any time soon.

* * *

 **Castiel.**

"Want a hand with that?" Cas padded across the kitchen in his fuzzy socks, pushing up the sleeves of the Christmas sweater Dean had bought him.

Dean smiled gratefully at him. "Thanks, Angel."

"No problem. You might need it now that we've got Bobby and Crowley to feed as well as my brothers." Cas began to empty sprouts onto the collection of plates that cluttered up the counter in front of them, letting his shoulders press against Dean's as they get to work serving up the Christmas dinner, nodding his head in time to the Christmas track that was currently playing from the speakers in the other room.

"Cas?" Dean began suddenly, breaking the comfortable quiet.

"Hm?"

"I know that this is water under the bridge and all that, but I gotta ask...why didn't you tell me? 'Bout havin' to go home early for work? I mean, I know you said about not wantin' Christmas to be awkward, but that just...doesn't feel like the only reason. Was there another reason?"

Cas was silent for a moment, before he nodded. "Yes. There was another reason."

"What was that?"

He paused in his routine. "I didn't want to say goodbye. Not just to you, but to Mary and John, Gabe and Sammy, Lawrence in general. I wasn't ready to go home yet. And I was worried that, if you had...y'know, asked me to stay, I wouldn't have been able to tell you no, regardless of my job. I didn't want to be forced to make that choice: I can't give up my career, but I didn't want to waste another chance with you. You see what I mean?"

"Yeah. I see exactly what you mean." Dean heaved out a breath, placing the carving knife down on the counter. "Look, Cas, I don't want to be left here and have to watch you skip town again."

"I understand, Dean -"

"Which is why I wanna come with you."

Cas almost dropped the saucepan in his hands. "You - What?"

"I want to come with you," Dean repeated. "Back to Pontiac. If you'll have me, of course."

"But - but -" Cas shook his head a little as he tried to muster up a complete sentence. "- But, what about your family? About the garage? About -?"

"Sammy and Gabe have got their own lives to live. They're gettin' married, maybe startin' a family of their own. They don't need me hangin' around here all the damn time - and I'm not havin' my baby brother leavin' home before I do." He rolled his eyes. "And I talked it over with Bobby earlier. Pulled him aside when Crowley was entertainin' you all with his business man lingo. He said that, if it's what I want, I should go for it, no matter how sad he is to see me go. He'll put in a good word for me with the garage in Pontiac where one of his old buddies works. Illinois has got plenty of cars to fix up after all." He flashed a smile at the younger Novak beside him. "So, what'cha think? You got room in your apartment for one more?"

"That depends." Cas returned the gesture with a smile of his own. "Are you willing to follow me all the way to Illinois?"

"Cas, I'd follow you all the way to the freakin' moon if I had to."

"Well, then." Cas rested the saucepan back on the counter and reached up to wrap his arms around Dean's neck, bringing their foreheads together. "I guess the answer has got to be yes, hasn't it?"

"Freakin' sap," Dean mumbled fondly.

"But I'm _your_ freaking sap," Cas replied.

"True, true. You are." Dean leaned in further, letting their lips meet, settling his hands on the small of Cas' back and rubbing soothing circles through the knitted sweater.

"Oh, Jesus Christ, guys, not in front of the food!" Jimmy's voice from the doorway prevented them from going any further. Cas smirked as he pulled away and caught sight of his twin brother's horrified expression.

"Yeah!" Sam chimed in, letting his head fall to rest on top of Gabriel's. "Get a room, you two!"

"I don't know what's worse," the blonde Novak commented. "Them fighting, or _this_."

Dean rolled his eyes, but kept his arm wrapped firmly around Cas. "Merry freakin' Christmas, Bumblebee."

Cas pulled his eyes away from the gathering at the kitchen door to smile up at the other man. "Merry Christmas, Dean."

* * *

 **The End.**

 **Phew! We got there, guys!**

 **Thank you so, so, so much to everyone who read/followed/favourited/reviewed this story! I love you all so much!**

 **I'll see you all soon for some more Destiel, my little sock puppets! Until then, Merry freakin' Christmas, and a happy New Year too! xx**


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